1999–2000 UEFA Cup first round

The following 96 teams participated in the first round.{{cite web |url=http://www.uefa.com/uefacup/news/index.asp?News=2339 |title=UEFA Cup: Club coefficients and draw details |publisher=UEFA |date=29 June 1999 |access-date=5 February 2025 |url-status=dead |archive-url=https://web.archive.org/web/20010725022042/http://www.uefa.com/uefacup/news/index.asp?News=2339 |archive-date=25 July 2001}}{{cite web |url=http://www.uefa.com/ucl/news/index.asp?News=2340 |title=UEFA Champions League: Club coefficients and draw details |publisher=UEFA |date=29 June 1999 |access-date=5 February 2025 |url-status=dead |archive-url=https://web.archive.org/web/20010725020829/http://www.uefa.com/ucl/news/index.asp?News=2340 |archive-date=25 July 2001}}{{cite web |last=Kassies |first=Bert |url=https://kassiesa.net/uefa/data/method2/trank1999.html |title=UEFA Team Ranking 1999 |publisher=UEFA European Cup Football |access-date=5 February 2025}}

|

|

|

|}

Notes

{{Cnote2 Begin|liststyle=disc}}

{{Cnote2|TH|n=0|^TH UEFA Cup title holders}}

{{Cnote2|QR|n=0|^QR Winners from the qualifying round}}

{{Cnote2|CL|n=0|^CL Losers from the Champions League third qualifying round}}

{{Cnote2|IC|n=0|^IC Teams qualified via the Intertoto Cup}}

{{Cnote2 End}}

The seeding groups were as follows:{{cite web |url=http://www.uefa.com/uefacup/news/index.asp?News=2618 |title=First Round Geographical Seeding Groups |publisher=UEFA |date=27 August 1999 |url-status=dead |archive-url=https://web.archive.org/web/20010502152232/http://www.uefa.com/uefacup/news/index.asp?News=2618 |archive-date=2 May 2001}}

{{Football box

|date = {{Start date|1999|9|14|df=y}}

|time = 18:00

|team1 = Steaua București {{fbaicon|ROU}}

|score = 2–0

|team2 = {{fbaicon|AUT}} LASK

|goals1 =

• Ciocoiu {{goal|63}}
• Dănciulescu {{goal|83}}

|goals2 =

|stadium = Stadionul Steaua, Bucharest

|attendance = 3,600

|referee = Steve Dunn (England)

|report = https://www.uefa.com/uefaeuropaleague/match/57032/

}}

{{Football box

|date = {{Start date|1999|9|28|df=y}}

|time = 18:00

|team1 = LASK {{fbaicon|AUT}}

|score = 2–3

|team2 = {{fbaicon|ROU}} Steaua București

|goals1 =

• Stumpf {{goal|6}}
• Sané {{goal|89}}

|goals2 =

• Bordeanu {{goal|8}}
• Ilie {{goal|30}}
• Duro {{goal|61}}

|stadium = Linzer Stadion, Linz

|attendance = 5,500

|referee = Arturo Daudén Ibáñez (Spain)

|report = https://www.uefa.com/uefaeuropaleague/match/57033/

}}

Steaua București won 5–2 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|14|df=y}}

|time = 18:00

|team1 = VfL Wolfsburg {{fbaicon|GER}}

|score = 2–0

|team2 = {{fbaicon|HUN}} Debrecen

|goals1 =

• Akonnor {{goal|61}}
• Juskowiak {{goal|87}}

|goals2 =

|stadium = VfL-Stadion, Wolfsburg

|attendance = 7,200

|referee = Mikko Vuorela (Finland)

|report = https://www.uefa.com/uefaeuropaleague/match/56978/

}}

{{Football box

|date = {{Start date|1999|9|28|df=y}}

|time = 18:00

|team1 = Debrecen {{fbaicon|HUN}}

|score = 2–1

|team2 = {{fbaicon|GER}} VfL Wolfsburg

|goals1 =

• Sabo {{goal|54||90}}

|goals2 =

• Akpoborie {{goal|25}}

|stadium = Stadion Oláh Gábor Út, Debrecen

|attendance = 4,500

|referee = John Rowbotham (Scotland)

|report = https://www.uefa.com/uefaeuropaleague/match/56979/

}}

VfL Wolfsburg won 3–2 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|14|df=y}}

|time = 16:00

|team1 = Red Star Belgrade {{fbaicon|FRY}}

|score = 0–1

|team2 = {{fbaicon|FRA|1974}} Montpellier

|goals1 =

|goals2 =

• Loko {{goal|6}}

|stadium = Georgi Asparuhov Stadium, Sofia, Bulgaria{{refn|group=note|name=FR Yugoslavia|Due to a flight embargo caused by sanctions resulting from the Kosovo War and NATO bombing of Yugoslavia, UEFA decided that, from the first round, Yugoslav teams were required to play their home matches at neutral venues until commercial flights resumed.{{cite web |url=http://news.bbc.co.uk/2/hi/sport/football/431722.stm |title=Sport: Football Leeds face trip into unknown |work=BBC Sport |date=27 August 1999 |access-date=17 February 2025}}{{cite web |last=Anderson |first=David |url=https://www.independent.ie/sport/belgrade-bother-for-leeds/26142422.html |title=Belgrade bother for Leeds |work=Irish Independent |date=27 August 1999 |access-date=17 February 2025}}}}

|attendance = 7,800

|referee = Dermot Gallagher (England)

|report = https://www.uefa.com/uefaeuropaleague/match/56962/

}}

{{Football box

|date = {{Start date|1999|9|28|df=y}}

|time = 18:00

|team1 = Montpellier {{fbaicon|FRA|1974}}

|score = 2–2

|team2 = {{fbaicon|FRY}} Red Star Belgrade

|goals1 =

• Ouédec {{goal|34}}
• Delaye {{goal|52}}

|goals2 =

• Jelić {{goal|48}}
• Bošković {{goal|55}}

|stadium = Stade de la Mosson, Montpellier

|attendance = 9,246

|referee = Livio Bazzoli (Italy)

|report = https://www.uefa.com/uefaeuropaleague/match/56963/

}}

Montpellier won 3–2 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|14|df=y}}

|time = 18:00

|team1 = Stabæk {{fbaicon|NOR}}

|score = 1–0

|team2 = {{fbaicon|ESP}} Deportivo La Coruña

|goals1 =

• Finstad {{goal|57}}

|goals2 =

|stadium = Ullevaal Stadion, Oslo

|attendance = 3,809

|referee = Romāns Lajuks (Latvia)

|report = https://www.uefa.com/uefaeuropaleague/match/57048/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 21:30

|team1 = Deportivo La Coruña {{fbaicon|ESP}}

|score = 2–0

|team2 = {{fbaicon|NOR}} Stabæk

|goals1 =

• Jokanović {{goal|37}}
• Conceição {{goal|63}}

|goals2 =

|stadium = Estadio Riazor, A Coruña

|attendance = 15,915

|referee = Kenny Clark (Scotland)

|report = https://www.uefa.com/uefaeuropaleague/match/57049/

}}

Deportivo La Coruña won 2–1 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 18:00

|team1 = Udinese {{fbaicon|ITA}}

|score = 1–0

|team2 = {{fbaicon|DEN}} AaB

|goals1 =

• Sottil {{goal|9}}

|goals2 =

|stadium = Stadio Friuli, Udine

|attendance = 17,661

|referee = Lubomír Puček (Czech Republic)

|report = https://www.uefa.com/uefaeuropaleague/match/57050/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 20:35

|team1 = AaB {{fbaicon|DEN}}

|score = 1–2

|team2 = {{fbaicon|ITA}} Udinese

|goals1 =

• Matovac {{goal|71}}

|goals2 =

• Muzzi {{goal|63}}
• Locatelli {{goal|90}}

|stadium = Aalborg Stadion, Aalborg

|attendance = 8,750

|referee = Dani Koren (Israel)

|report = https://www.uefa.com/uefaeuropaleague/match/57051/

}}

Udinese won 3–1 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|14|df=y}}

|time = 17:30

|team1 = Partizan {{fbaicon|FRY}}

|score = 1–3

|team2 = {{fbaicon|ENG}} Leeds United

|goals1 =

• Tomić {{goal|20}}

|goals2 =

• Bowyer {{goal|26||82}}
• Radebe {{goal|39}}

|stadium = Abe Lenstra Stadion, Heerenveen, Netherlands{{refn|group=note|name=FR Yugoslavia}}

|attendance = 4,950

|referee = Herbert Fandel (Germany)

|report = https://www.uefa.com/uefaeuropaleague/match/56966/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 21:00

|team1 = Leeds United {{fbaicon|ENG}}

|score = 1–0

|team2 = {{fbaicon|FRY}} Partizan

|goals1 =

• Huckerby {{goal|55}}

|goals2 =

|stadium = Elland Road, Leeds

|attendance = 39,806

|referee = Fritz Stuchlik (Austria)

|report = https://www.uefa.com/uefaeuropaleague/match/56967/

}}

Leeds United won 4–1 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|15|df=y}}

|time = 18:00

|team1 = HJK {{fbaicon|FIN}}

|score = 0–1

|team2 = {{fbaicon|FRA|1974}} Lyon

|goals1 =

|goals2 =

• Vairelles {{goal|16}}

|stadium = Helsinki Olympic Stadium, Helsinki

|attendance = 8,103

|referee = Michal Beneš (Czech Republic)

|report = https://www.uefa.com/uefaeuropaleague/match/57008/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 20:45

|team1 = Lyon {{fbaicon|FRA|1974}}

|score = 5–1

|team2 = {{fbaicon|FIN}} HJK

|goals1 =

• Anderson {{goal|11}}
• Blanc {{goal|15}}
• Linarès {{goal|18}}
• Vairelles {{goal|70||86}}

|goals2 =

• Lehkosuo {{goal|40}}

|stadium = Stade de Gerland, Lyon

|attendance = 15,016

|referee = Edo Trivković (Croatia)

|report = https://www.uefa.com/uefaeuropaleague/match/57009/

}}

Lyon won 6–1 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|15|df=y}}

|time = 21:30

|team1 = Atlético Madrid {{fbaicon|ESP}}

|score = 3–0

|team2 = {{fbaicon|TUR}} Ankaragücü

|goals1 =

• Gamarra {{goal|43}}
• Hasselbaink {{goal|43}}
• Paunović {{goal|58}}

|goals2 =

|stadium = Vicente Calderón Stadium, Madrid

|attendance = 11,600

|referee = Georg Dardenne (Germany)

|report = https://www.uefa.com/uefaeuropaleague/match/56984/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 18:30

|team1 = Ankaragücü {{fbaicon|TUR}}

|score = 1–0

|team2 = {{fbaicon|ESP}} Atlético Madrid

|goals1 =

• Aksancak {{goal|85}}

|goals2 =

|stadium = Ankara 19 Mayıs Stadium, Ankara

|attendance = 1,700

|referee = Claus Bo Larsen (Denmark)

|report = https://www.uefa.com/uefaeuropaleague/match/56985/

}}

Atlético Madrid won 3–1 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 21:30

|team1 = MTK Hungária {{fbaicon|HUN}}

|score = 0–0

|team2 = {{fbaicon|TUR}} Fenerbahçe

|goals1 =

|goals2 =

|stadium = Hidegkuti Nándor Stadium, Budapest

|attendance = 2,950

|referee = Miro Ukalovic (Sweden)

|report = https://www.uefa.com/uefaeuropaleague/match/57018/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 19:30

|team1 = Fenerbahçe {{fbaicon|TUR}}

|score = 0–2

|team2 = {{fbaicon|HUN}} MTK Hungária

|goals1 =

|goals2 =

• Kenesei {{goal|56||60}}

|stadium = Şükrü Saracoğlu Stadium, Istanbul

|attendance = 13,000

|referee = Lutz Michael Fröhlich (Germany)

|report = https://www.uefa.com/uefaeuropaleague/match/57019/

}}

MTK Hungária won 2–0 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 20:00

|team1 = Anderlecht {{fbaicon|BEL}}

|score = 3–1

|team2 = {{fbaicon|SVN}} Olimpija Ljubljana

|goals1 =

• Bajrektarevič {{goal|20|o.g.}}
• Radzinski {{goal|35||66}}

|goals2 =

• Ekmečič {{goal|52}}

|stadium = Constant Vanden Stock Stadium, Brussels

|attendance = 14,157

|referee = Muhittin Boşat (Turkey)

|report = https://www.uefa.com/uefaeuropaleague/match/57002/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 20:00

|team1 = Olimpija Ljubljana {{fbaicon|SVN}}

|score = 0–3

|team2 = {{fbaicon|BEL}} Anderlecht

|goals1 =

|goals2 =

• Koller {{goal|64}}
• Radzinski {{goal|69||72}}

|stadium = Bežigrad Stadium, Ljubljana

|attendance = 800

|referee = Yuri Baskakov (Russia)

|report = https://www.uefa.com/uefaeuropaleague/match/57003/

}}

Anderlecht won 6–1 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 18:30

|team1 = Roda JC {{fbaicon|NED}}

|score = 2–0

|team2 = {{fbaicon|UKR}} Shakhtar Donetsk

|goals1 =

• Doomernik {{goal|20}}
• Zafarin {{goal|25}}

|goals2 =

|stadium = Gemeentelijk Sportpark Kaalheide, Kerkrade

|attendance = 6,635

|referee = John Ferry (Northern Ireland)

|report = https://www.uefa.com/uefaeuropaleague/match/57036/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 17:30

|team1 = Shakhtar Donetsk {{fbaicon|UKR}}

|score = 1–3

|team2 = {{fbaicon|NED}} Roda JC

|goals1 =

• Benyo {{goal|32}}

|goals2 =

• Tchoutang {{goal|27}}
• van der Luer {{goal|81}}
• van Dessel {{goal|87}}

|stadium = Shakhtar Stadium, Donetsk

|attendance = 19,526

|referee = Metin Tokat (Turkey)

|report = https://www.uefa.com/uefaeuropaleague/match/57037/

}}

Roda JC won 5–1 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 18:00

|team1 = Bodø/Glimt {{fbaicon|NOR}}

|score = 0–5

|team2 = {{fbaicon|GER}} Werder Bremen

|goals1 =

|goals2 =

• Pizarro {{goal|12||75}}
• Bogdanović {{goal|44||54}}
• Maksymov {{goal|59}}

|stadium = Lerkendal Stadion, Trondheim

|attendance = 1,425

|referee = Ihor Yarmenchuk (Ukraine)

|report = https://www.uefa.com/uefaeuropaleague/match/56968/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 20:00

|team1 = Werder Bremen {{fbaicon|GER}}

|score = 1–1

|team2 = {{fbaicon|NOR}} Bodø/Glimt

|goals1 =

• Aílton {{goal|76}}

|goals2 =

• Staurvik {{goal|36}}

|stadium = Weserstadion, Bremen

|attendance = 15,291

|referee = Orhan Erdemir (Turkey)

|report = https://www.uefa.com/uefaeuropaleague/match/56969/

}}

Werder Bremen won 6–1 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 20:00

|team1 = Viking {{fbaicon|NOR}}

|score = 3–0

|team2 = {{fbaicon|POR}} Sporting CP

|goals1 =

• Svensson {{goal|57}}
• Berre {{goal|69}}
• Espevoll {{goal|77|pen.}}

|goals2 =

|stadium = Viking Stadion, Stavanger

|attendance = 4,080

|referee = Fiorenzo Treossi (Italy)

|report = https://www.uefa.com/uefaeuropaleague/match/57020/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 20:00

|team1 = Sporting CP {{fbaicon|POR}}

|score = 1–0

|team2 = {{fbaicon|NOR}} Viking

|goals1 =

• Ayew {{goal|71}}

|goals2 =

|stadium = Estádio José Alvalade, Lisbon

|attendance = 17,000

|referee = Marcel Lica (Romania)

|report = https://www.uefa.com/uefaeuropaleague/match/57021/

}}

Viking won 3–1 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 17:00

|team1 = Maccabi Tel Aviv {{fbaicon|ISR}}

|score = 2–2

|team2 = {{fbaicon|FRA|1974}} Lens

|goals1 =

• Kubica {{goal|43}}
• Dayan {{goal|75}}

|goals2 =

• Sakho {{goal|38}}
• Job {{goal|55}}

|stadium = Ramat Gan Stadium, Ramat Gan

|attendance = 2,500

|referee = Ivan Dobrinov (Bulgaria)

|report = https://www.uefa.com/uefaeuropaleague/match/56986/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 18:00

|team1 = Lens {{fbaicon|FRA|1974}}

|score = 2–1

|team2 = {{fbaicon|ISR}} Maccabi Tel Aviv

|goals1 =

• Nouma {{goal|77}}
• Delporte {{goal|80}}

|goals2 =

• Basis {{goal|24}}

|stadium = Stade Félix-Bollaert, Lens

|attendance = 35,663

|referee = Manuel Mejuto González (Spain)

|report = https://www.uefa.com/uefaeuropaleague/match/56987/

}}

Lens won 4–3 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 20:30

|team1 = 1. FC Kaiserslautern {{fbaicon|GER}}

|score = 3–0

|team2 = {{fbaicon|SCO}} Kilmarnock

|goals1 =

• Koch {{goal|29}}
• Djorkaeff {{goal|75}}
• Marschall {{goal|39}}

|goals2 =

|stadium = Fritz-Walter-Stadion, Kaiserslautern

|attendance = 21,000

|referee = Jorge Coroado (Portugal)

|report = https://www.uefa.com/uefaeuropaleague/match/57038/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 18:00

|team1 = Kilmarnock {{fbaicon|SCO}}

|score = 0–2

|team2 = {{fbaicon|GER}} 1. FC Kaiserslautern

|goals1 =

|goals2 =

• Djorkaeff {{goal|22}}
• Ramzy {{goal|29}}

|stadium = Rugby Park, Kilmarnock

|attendance = 8,050

|referee = Costas Kapitanis (Cyprus)

|report = https://www.uefa.com/uefaeuropaleague/match/57039/

}}

Kilmarnock won 5–0 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 19:00

|team1 = Helsingborgs IF {{fbaicon|SWE}}

|score = 1–1

|team2 = {{fbaicon|UKR}} Karpaty Lviv

|goals1 =

• Jonson {{goal|85}}

|goals2 =

• Hetsko {{goal|17}}

|stadium = Olympia, Helsingborg

|attendance = 3,642

|referee = William Young (Scotland)

|report = https://www.uefa.com/uefaeuropaleague/match/56970/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 18:00

|team1 = Karpaty Lviv {{fbaicon|UKR}}

|score = 1–1

|aet = yes

|team2 = {{fbaicon|SWE}} Helsingborgs IF

|goals1 =

• Hetsko {{goal|90+2}}

|goals2 =

• Jonson {{goal|90}}

|stadium = Ukraina Stadium, Lviv

|attendance = 26,150

|referee = Vladimír Hriňák (Slovakia)

|penalties1 =

• Hetsko {{penmiss}}
• Yevtushok {{penmiss}}
• Mizin {{pengoal}}
• Pavliukh {{pengoal}}

|penaltyscore = 2–4

|penalties2 =

• {{pengoal}} Jansson
• {{pengoal}} R. Nilsson
• {{penmiss}} Jonson
• {{pengoal}} Markstedt
• {{pengoal}} Jakobsson

|report = https://www.uefa.com/uefaeuropaleague/match/56971/

}}

2–2 on aggregate; Helsingborgs IF won 4–2 on penalties.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 19:00

|team1 = Lech Poznań {{fbaicon|POL}}

|score = 1–2

|team2 = {{fbaicon|SWE}} IFK Göteborg

|goals1 =

• Żurawski {{goal|44|pen.}}

|goals2 =

• Andersson {{goal|27}}
• Mild {{goal|83}}

|stadium = Stadion Poznań, Poznań

|attendance = 5,000

|referee = Zoran Arsić (FR Yugoslavia)

|report = https://www.uefa.com/uefaeuropaleague/match/57004/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 19:00

|team1 = IFK Göteborg {{fbaicon|SWE}}

|score = 0–0

|team2 = {{fbaicon|POL}} Lech Poznań

|goals1 =

|goals2 =

|stadium = Ullevi, Gothenburg

|attendance = 4,910

|referee = Andreas Schluchter (Switzerland)

|report = https://www.uefa.com/uefaeuropaleague/match/57005/

}}

IFK Göteborg won 2–1 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 19:15

|team1 = Teplice {{fbaicon|CZE}}

|score = 3–1

|team2 = {{fbaicon|HUN}} Ferencváros

|goals1 =

• Frýdek {{goal|33}}
• Kolomazník {{goal|54}}
• Rízek {{goal|71}}

|goals2 =

• Tóth {{goal|15}}

|stadium = Na Stínadlech, Teplice

|attendance = 10,258

|referee = Massimo Busacca (Switzerland)

|report = https://www.uefa.com/uefaeuropaleague/match/56980/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 18:00

|team1 = Ferencváros {{fbaicon|HUN}}

|score = 1–1

|team2 = {{fbaicon|CZE}} Teplice

|goals1 =

• Mátyus {{goal|57|pen.}}

|goals2 =

• Rada {{goal|53}}

|stadium = Üllői úti stadion, Budapest

|attendance = 8,534

|referee = Jacek Granat (Poland)

|report = https://www.uefa.com/uefaeuropaleague/match/56981/

}}

Teplice won 4–2 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 20:45

|team1 = CSKA Sofia {{fbaicon|BUL}}

|score = 0–2

|team2 = {{fbaicon|ENG}} Newcastle United

|goals1 =

|goals2 =

• Solano {{goal|51}}
• Ketsbaia {{goal|77}}

|stadium = Balgarska Armiya Stadium, Sofia

|attendance = 20,300

|referee = Juan Rocca (Spain)

|report = https://www.uefa.com/uefaeuropaleague/match/57014/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 20:00

|team1 = Newcastle United {{fbaicon|ENG}}

|score = 2–2

|team2 = {{fbaicon|BUL}} CSKA Sofia

|goals1 =

• Shearer {{goal|36}}
• Robinson {{goal|88}}

|goals2 =

• Litera {{goal|29}}
• Simeonov {{goal|90}}

|stadium = St James' Park, Newcastle upon Tyne

|attendance = 36,228

|referee = Luc Huyghe (Belgium)

|report = https://www.uefa.com/uefaeuropaleague/match/57015/

}}

Newcastle United won 4–2 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 16:00

|team1 = HIT Gorica {{fbaicon|SVN}}

|score = 0–1

|team2 = {{fbaicon|GRE}} Panathinaikos

|goals1 =

|goals2 =

• Liberopoulos {{goal|14}}

|stadium = Sports Park, Nova Gorica

|attendance = 1,700

|referee = Eyal Zur (Israel)

|report = https://www.uefa.com/uefaeuropaleague/match/57030/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 20:15

|team1 = Panathinaikos {{fbaicon|GRE}}

|score = 2–0

|team2 = {{fbaicon|SVN}} HIT Gorica

|goals1 =

• Sigurðsson {{goal|38}}
• Nasiopoulos {{goal|69}}

|goals2 =

|stadium = Olympic Stadium, Athens

|attendance = 6,280

|referee = Wolfgang Stark (Germany)

|report = https://www.uefa.com/uefaeuropaleague/match/57031/

}}

Panathinaikos won 3–0 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 21:00

|team1 = Amica Wronki {{fbaicon|POL}}

|score = 2–0

|team2 = {{fbaicon|DEN}} Brøndby

|goals1 =

• Dawidowski {{goal|22}}
• Bosacki {{goal|69}}

|goals2 =

|stadium = Stadion Amica, Wronki

|attendance = 2,863

|referee = Ceri Richards (Wales)

|report = https://www.uefa.com/uefaeuropaleague/match/56998/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 18:30

|team1 = Brøndby {{fbaicon|DEN}}

|score = 4–3

|team2 = {{fbaicon|POL}} Amica Wronki

|goals1 =

• Madsen {{goal|35||76}}
• Vragel {{goal|54}}
• Christensen {{goal|78}}

|goals2 =

• Kryszałowicz {{goal|52||68}}
• Kukiełka {{goal|63|pen.}}

|stadium = Brøndby Stadium, Brøndbyvester

|attendance = 5,907

|referee = Gylfi Orrason (Iceland)

|report = https://www.uefa.com/uefaeuropaleague/match/56999/

}}

Amica Wronki won 5–4 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 21:30

|team1 = Beira-Mar {{fbaicon|POR}}

|score = 1–2

|team2 = {{fbaicon|NED}} Vitesse

|goals1 =

• Faye {{goal|41}}

|goals2 =

• Van Hooijdonk {{goal|50}}
• Grozdić {{goal|82}}

|stadium = Estádio Mário Duarte, Aveiro

|attendance = 3,500

|referee = Andreas Georgiou (Cyprus)

|report = https://www.uefa.com/uefaeuropaleague/match/56988/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 21:00

|team1 = Vitesse {{fbaicon|NED}}

|score = 0–0

|team2 = {{fbaicon|POR}} Beira-Mar

|goals1 =

|goals2 =

|stadium = GelreDome, Arnhem

|attendance = 13,650

|referee = Roland Beck (Liechtenstein)

|report = https://www.uefa.com/uefaeuropaleague/match/56989/

}}

Vitesse won 2–0 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 20:30

|team1 = GAK {{fbaicon|AUT}}

|score = 3–0

|team2 = {{fbaicon|SVK}} Spartak Trnava

|goals1 =

• Akwuegbu {{goal|12||56}}
• Adu {{goal|34}}

|goals2 =

|stadium = Arnold Schwarzenegger Stadium, Graz

|attendance = 3,070

|referee = Tom Henning Øvrebø (Norway)

|report = https://www.uefa.com/uefaeuropaleague/match/57022/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 18:00

|team1 = Spartak Trnava {{fbaicon|SVK}}

|score = 2–1

|team2 = {{fbaicon|AUT}} GAK

|goals1 =

• Mužlay {{goal|45||70}}

|goals2 =

• Standfest {{goal|14}}

|stadium = Štadión Antona Malatinského, Trnava

|attendance = 2,000

|referee = Eric Blareau (Belgium)

|report = https://www.uefa.com/uefaeuropaleague/match/57023/

}}

GAK won 4–2 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 17:45

|team1 = Hajduk Split {{fbaicon|CRO}}

|score = 0–0

|team2 = {{fbaicon|BUL}} Levski Sofia

|goals1 =

|goals2 =

|stadium = Stadion Poljud, Split

|attendance = 11,627

|referee = Pasquale Rodomonti (Italy)

|report = https://www.uefa.com/uefaeuropaleague/match/57040/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 14:45

|team1 = Levski Sofia {{fbaicon|BUL}}

|score = 3–0

|team2 = {{fbaicon|CRO}} Hajduk Split

|goals1 =

• Ivankov {{goal|16|pen.}}
• Bachev {{goal|33}}
• Dimitrov {{goal|85}}

|goals2 =

|stadium = Georgi Asparuhov Stadium, Sofia

|attendance = 24,000

|referee = Michael Riley (England)

|report = https://www.uefa.com/uefaeuropaleague/match/57041/

}}

Levski Sofia won 3–0 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 20:30

|team1 = Celtic {{fbaicon|SCO}}

|score = 2–0

|team2 = {{fbaicon|ISR}} Hapoel Tel Aviv

|goals1 =

• Larsson {{goal|25||50|pen.}}

|goals2 =

|stadium = Celtic Park, Glasgow

|attendance = 45,171

|referee = Frank De Bleeckere (Belgium)

|report = https://www.uefa.com/uefaeuropaleague/match/57006/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 20:45

|team1 = Hapoel Tel Aviv {{fbaicon|ISR}}

|score = 0–1

|team2 = {{fbaicon|SCO}} Celtic

|goals1 =

|goals2 =

• Larsson {{goal|63}}

|stadium = Bloomfield Stadium, Tel Aviv

|attendance = 6,400

|referee = Juan Manuel Brito Arceo (Spain)

|report = https://www.uefa.com/uefaeuropaleague/match/57007/

}}

Celtic won 3–0 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 20:15

|team1 = Lausanne-Sports {{fbaicon|SUI}}

|score = 3–2

|team2 = {{fbaicon|ESP}} Celta Vigo

|goals1 =

• Kuzba {{goal|20}}
• Mazzoni {{goal|21||57}}

|goals2 =

• Revivo {{goal|62}}
• Karpin {{goal|66|pen.}}

|stadium = Olympique de la Pontaise, Lausanne

|attendance = 7,770

|referee = Gary Willard (England)

|report = https://www.uefa.com/uefaeuropaleague/match/56972/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 20:00

|team1 = Celta Vigo {{fbaicon|ESP}}

|score = 4–0

|team2 = {{fbaicon|SUI}} Lausanne-Sports

|goals1 =

• McCarthy {{goal|11||84||90+2}}
• Mostovoi {{goal|76}}

|goals2 =

|stadium = Balaídos, Vigo

|attendance = 12,840

|referee = Stéphane Bré (France)

|report = https://www.uefa.com/uefaeuropaleague/match/56973/

}}

Celta Vigo won 6–3 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 19:30

|team1 = Ionikos {{fbaicon|GRE}}

|score = 1–3

|team2 = {{fbaicon|FRA|1974}} Nantes

|goals1 =

• Dimitriadis {{goal|90}}

|goals2 =

• Lièvre {{goal|56}}
• Monterrubio {{goal|67||83}}

|stadium = Olympic Stadium, Athens

|attendance = 1,335

|referee = Manfred Schüttengruber (Austria)

|report = https://www.uefa.com/uefaeuropaleague/match/57024/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 19:00

|team1 = Nantes {{fbaicon|FRA|1974}}

|score = 1–0

|team2 = {{fbaicon|GRE}} Ionikos

|goals1 =

• Da Rocha {{goal|48}}

|goals2 =

|stadium = Stade de la Beaujoire, Nantes

|attendance = 18,522

|referee = Morgan Norman (Sweden)

|report = https://www.uefa.com/uefaeuropaleague/match/57025/

}}

Nantes won 4–1 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 20:00

|team1 = Aris {{fbaicon|GRE}}

|score = 1–1

|team2 = {{fbaicon|SUI}} Servette

|goals1 =

• Mantzios {{goal|11}}

|goals2 =

• Petrov {{goal|88}}

|stadium = Kleanthis Vikelidis Stadium, Thessaloniki

|attendance = 17,127

|referee = Knud Erik Fisker (Denmark)

|report = https://www.uefa.com/uefaeuropaleague/match/56956/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 20:30

|team1 = Servette {{fbaicon|SUI}}

|score = 1–2

|aet = yes

|team2 = {{fbaicon|GRE}} Aris

|goals1 =

• Lonfat {{goal|35}}

|goals2 =

• Paulo Andrioli {{goal|37}}
• Kyzeridis {{goal|97}}

|stadium = Charmilles Stadium, Geneva

|attendance = 5,228

|referee = René Temmink (Netherlands)

|report = https://www.uefa.com/uefaeuropaleague/match/56957/

}}

Aris won 3–2 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 20:45

|team1 = Monaco {{fbaicon|FRA|1974}}

|score = 3–0

|team2 = {{fbaicon|SCO}} St Johnstone

|goals1 =

• Simone {{goal|69||89}}
• Trezeguet {{goal|72}}

|goals2 =

|stadium = Stade Louis II, Monaco

|attendance = 7,881

|referee = Edgar Steinborn (Germany)

|report = https://www.uefa.com/uefaeuropaleague/match/56990/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 20:45

|team1 = St Johnstone {{fbaicon|SCO}}

|score = 3–3

|team2 = {{fbaicon|FRA|1974}} Monaco

|goals1 =

• Griffin {{goal|24|pen.}}
• Dasovic {{goal|33}}
• O'Neil {{goal|75}}

|goals2 =

• Léonard {{goal|4|pen.}}
• Pršo {{goal|9}}
• Legwinski {{goal|69}}

|stadium = McDiarmid Park, Perth

|attendance = 7,706

|referee = Victor José Esquinas Torres (Spain)

|report = https://www.uefa.com/uefaeuropaleague/match/56991/

}}

Monaco won 6–3 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 18:30

|team1 = Inter Bratislava {{fbaicon|SVK}}

|score = 1–0

|team2 = {{fbaicon|AUT}} Rapid Wien

|goals1 =

• Ľalík {{goal|45}}

|goals2 =

|stadium = Štadión Pasienky, Bratislava

|attendance = 6,596

|referee = Pascal Garibian (France)

|report = https://www.uefa.com/uefaeuropaleague/match/56958/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 21:30

|team1 = Rapid Wien {{fbaicon|AUT}}

|score = 1–2

|team2 = {{fbaicon|SVK}} Inter Bratislava

|goals1 =

• Zingler {{goal|65}}

|goals2 =

• Suchancok {{goal|45}}
• Babnič {{goal|64}}

|stadium = Gerhard Hanappi Stadium, Vienna

|attendance = 6,068

|referee = Valentin Ivanov (Russia)

|report = https://www.uefa.com/uefaeuropaleague/match/56959/

}}

Inter Bratislava won 3–1 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 18:30

|team1 = Lyngby {{fbaicon|DEN}}

|score = 1–2

|team2 = {{fbaicon|RUS}} Lokomotiv Moscow

|goals1 =

• Arifullin {{goal|69|o.g.}}

|goals2 =

• Chugaynov {{goal|13}}
• Bulykin {{goal|37}}

|stadium = Lyngby Stadium, Lyngby

|attendance = 1,500

|referee = Dick van Egmond (Netherlands)

|report = https://www.uefa.com/uefaeuropaleague/match/57042/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 18:00

|team1 = Lokomotiv Moscow {{fbaicon|RUS}}

|score = 3–0

|team2 = {{fbaicon|DEN}} Lyngby

|goals1 =

• Kharlachev {{goal|20}}
• Drozdov {{goal|43}}
• Janashia {{goal|44}}

|goals2 =

|stadium = Lokomotiv Stadium, Moscow

|attendance = 7,500

|referee = Milan Mitrović (Slovenia)

|report = https://www.uefa.com/uefaeuropaleague/match/57043/

}}

Lokomotiv Moscow won 5–1 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 17:30

|team1 = Skonto {{fbaicon|LVA}}

|score = 1–0

|team2 = {{fbaicon|POL}} Widzew Łódź

|goals1 =

• Astafjevs {{goal|31}}

|goals2 =

|stadium = Daugava Stadium, Riga

|attendance = 780

|referee = Jon Skjervold (Norway)

|report = https://www.uefa.com/uefaeuropaleague/match/56974/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 18:00

|team1 = Widzew Łódź {{fbaicon|POL}}

|score = 2–0

|team2 = {{fbaicon|LVA}} Skonto

|goals1 =

• Wichniarek {{goal|1}}
• Gęsior {{goal|43}}

|goals2 =

|stadium = Stadion Widzewa, Łódź

|attendance = 4,000

|referee = Kristinn Jakobsson (Iceland)

|report = https://www.uefa.com/uefaeuropaleague/match/56975/

}}

Widzew Łódź won 2–1 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 21:30

|team1 = Roma {{fbaicon|ITA}}

|score = 7–0

|team2 = {{fbaicon|POR}} Vitória de Setúbal

|goals1 =

• Aldair {{goal|12}}
• Montella {{goal|13}}
• Alenichev {{goal|15||54||75}}
• Assunção {{goal|39}}
• Delvecchio {{goal|73}}

|goals2 =

|stadium = Stadio Olimpico, Rome

|attendance = 23,013

|referee = Vasili Melnychuk (Ukraine)

|report = https://www.uefa.com/uefaeuropaleague/match/57000/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 22:30

|team1 = Vitória de Setúbal {{fbaicon|POR}}

|score = 1–0

|team2 = {{fbaicon|ITA}} Roma

|goals1 =

• Makinwa {{goal|79}}

|goals2 =

|stadium = Estádio do Bonfim, Setúbal

|attendance = 3,500

|referee = Dieter Schoch (Switzerland)

|report = https://www.uefa.com/uefaeuropaleague/match/57001/

}}

Roma won 7–1 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 19:15

|team1 = Parma {{fbaicon|ITA}}

|score = 3–2

|team2 = {{fbaicon|UKR}} Kryvbas Kryvyi Rih

|goals1 =

• Di Vaio {{goal|13||20}}
• Baggio {{goal|67}}

|goals2 =

• Palyanytsya {{goal|5}}
• Monaryov {{goal|74}}

|stadium = Stadio Ennio Tardini, Parma

|attendance = 3,887

|referee = Stuart Dougal (Scotland)

|report = https://www.uefa.com/uefaeuropaleague/match/56976/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 18:00

|team1 = Kryvbas Kryvyi Rih {{fbaicon|UKR}}

|score = 0–3

|team2 = {{fbaicon|ITA}} Parma

|goals1 =

|goals2 =

• Boghossian {{goal|36}}
• Crespo {{goal|40}}
• Di Vaio {{goal|67}}

|stadium = Metalurh Stadium, Kryvyi Rih

|attendance = 28,000

|referee = Konrad Plautz (Austria)

|report = https://www.uefa.com/uefaeuropaleague/match/56977/

}}

Parma won 6–2 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 19:15

|team1 = Hapoel Haifa {{fbaicon|ISR}}

|score = 3–1

|team2 = {{fbaicon|BEL}} Club Brugge

|goals1 =

• Turgeman {{goal|18||32}}
• Sivilia {{goal|44}}

|goals2 =

• Jankauskas {{goal|65}}

|stadium = Kiryat Eliezer Stadium, Haifa

|attendance = 6,000

|referee = Constantin Zotta (Romania)

|report = https://www.uefa.com/uefaeuropaleague/match/57026/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 20:30

|team1 = Club Brugge {{fbaicon|BEL}}

|score = 4–2

|team2 = {{fbaicon|ISR}} Hapoel Haifa

|goals1 =

• Verheyen {{goal|20}}
• Borkelmans {{goal|25}}
• Janssen {{goal|52||90}}

|goals2 =

• Roso {{goal|18}}
• Turgeman {{goal|78}}

|stadium = Olympiastadion, Brugge

|attendance = 8,747

|referee = Roy Helge Olsen (Norway)

|report = https://www.uefa.com/uefaeuropaleague/match/57027/

}}

5–5 on aggregate; Hapoel Haifa won on away goals.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 14:00

|team1 = Torpedo Kutaisi {{fbaicon|GEO|1990}}

|score = 0–1

|team2 = {{fbaicon|GRE}} AEK Athens

|goals1 =

|goals2 =

• Zikos {{goal|90+1}}

|stadium = Ramaz Shengelia Stadium, Kutaisi

|attendance = 7,100

|referee = John McDermott (Republic of Ireland)

|report = https://www.uefa.com/uefaeuropaleague/match/56992/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 16:00

|team1 = AEK Athens {{fbaicon|GRE}}

|score = 6–1

|team2 = {{fbaicon|GEO|1990}} Torpedo Kutaisi

|goals1 =

• Ćirić {{goal|8|pen.}}
• Bjeković {{goal|22}}
• Maladenis {{goal|24}}
• Kopitsis {{goal|44||88}}
• Nikolaidis {{goal|73}}

|goals2 =

• Megreladze {{goal|72}}

|stadium = Nea Smyrni Stadium, Athens

|attendance = 4,008

|referee = Miroslav Liba (Czech Republic)

|report = https://www.uefa.com/uefaeuropaleague/match/56993/

}}

AEK Athens won 7–1 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 20:00

|team1 = Omonia {{fbaicon|CYP|1960}}

|score = 2–5

|team2 = {{fbaicon|ITA}} Juventus

|goals1 =

• Kontolefteros {{goal|75||86}}

|goals2 =

• Inzaghi {{goal|2||17}}
• Kovačević {{goal|22}}
• Esnáider {{goal|24}}
• Del Piero {{goal|82}}

|stadium = Makario Stadium, Nicosia

|attendance = 12,485

|referee = Sergey Shmolik (Belarus)

|report = https://www.uefa.com/uefaeuropaleague/match/56960/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 20:30

|team1 = Juventus {{fbaicon|ITA}}

|score = 5–0

|team2 = {{fbaicon|CYP|1960}} Omonia

|goals1 =

• Kovačević {{goal|21||47||86}}
• Tacchinardi {{goal|55}}
• Conte {{goal|90}}

|goals2 =

|stadium = Stadio La Favorita, Palermo

|attendance = 27,527

|referee = Sorin Corpodean (Romania)

|report = https://www.uefa.com/uefaeuropaleague/match/56961/

}}

Juventus won 10–2 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 21:00

|team1 = West Ham United {{fbaicon|ENG}}

|score = 3–0

|team2 = {{fbaicon|CRO}} Osijek

|goals1 =

• Wanchope {{goal|39}}
• Di Canio {{goal|48}}
• Lampard {{goal|58}}

|goals2 =

|stadium = Boleyn Ground, London

|attendance = 25,331

|referee = Paulo Paraty (Portugal)

|report = https://www.uefa.com/uefaeuropaleague/match/56994/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 21:00

|team1 = Osijek {{fbaicon|CRO}}

|score = 1–3

|team2 = {{fbaicon|ENG}} West Ham United

|goals1 =

• Bubalo {{goal|70}}

|goals2 =

• Kitson {{goal|27}}
• Ruddock {{goal|83}}
• Foé {{goal|90}}

|stadium = Stadion Gradski vrt, Osijek

|attendance = 7,700

|referee = Jack van Hulten (Netherlands)

|report = https://www.uefa.com/uefaeuropaleague/match/56995/

}}

West Ham United won 6–1 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 16:30

|team1 = Vojvodina {{fbaicon|FRY}}

|score = 0–0

|team2 = {{fbaicon|CZE}} Slavia Prague

|goals1 =

|goals2 =

|stadium = Gradski stadion, Skopje, Macedonia{{refn|group=note|name=FR Yugoslavia}}

|attendance = 700

|referee = Roelof Luinge (Netherlands)

|report = https://www.uefa.com/uefaeuropaleague/match/57044/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 17:00

|team1 = Slavia Prague {{fbaicon|CZE}}

|score = 3–2

|team2 = {{fbaicon|FRY}} Vojvodina

|goals1 =

• Petrouš {{goal|40}}
• Došek {{goal|74}}
• Zelenka {{goal|80}}

|goals2 =

• Belić {{goal|18}}
• Bogdanović {{goal|47}}

|stadium = Stadion Evžena Rošického, Prague

|attendance = 3,170

|referee = Domenico Messina (Italy)

|report = https://www.uefa.com/uefaeuropaleague/match/57045/

}}

Slavia Prague won 3–2 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 16:50

|team1 = Sigma Olomouc {{fbaicon|CZE}}

|score = 1–3

|team2 = {{fbaicon|ESP}} Mallorca

|goals1 =

• Kobylík {{goal|63}}

|goals2 =

• Engonga {{goal|12}}
• Tristán {{goal|53}}
• Stanković {{goal|76}}

|stadium = Andrův stadion, Olomouc

|attendance = 4,020

|referee = Leif Sundell (Sweden)

|report = https://www.uefa.com/uefaeuropaleague/match/57010/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 21:30

|team1 = Mallorca {{fbaicon|ESP}}

|score = 0–0

|team2 = {{fbaicon|CZE}} Sigma Olomouc

|goals1 =

|goals2 =

|stadium = San Moix, Palma de Mallorca

|attendance = 12,640

|referee = Giorgos Bikas (Greece)

|report = https://www.uefa.com/uefaeuropaleague/match/57011/

}}

Mallorca won 3–1 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 22:15

|team1 = Benfica {{fbaicon|POR}}

|score = 0–1

|team2 = {{fbaicon|ROU}} Dinamo București

|goals1 =

|goals2 =

• Năstase {{goal|35}}

|stadium = Estádio da Luz, Lisbon

|attendance = 31,000

|referee = Sándor Puhl (Hungary)

|report = https://www.uefa.com/uefaeuropaleague/match/57016/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 19:45

|team1 = Dinamo București {{fbaicon|ROU}}

|score = 0–2

|team2 = {{fbaicon|POR}} Benfica

|goals1 =

|goals2 =

• Maniche {{goal|25}}
• Chano {{goal|72}}

|stadium = Stadionul Național, Bucharest

|attendance = 11,144

|referee = Alan Snoddy (Northern Ireland)

|report = https://www.uefa.com/uefaeuropaleague/match/57017/

}}

Benfica won 2–1 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 20:30

|team1 = Ajax {{fbaicon|NED}}

|score = 6–1

|team2 = {{fbaicon|SVK}} Dukla Banská Bystrica

|goals1 =

• Verlaat {{goal|25|pen.}}
• Reuser {{goal|26}}
• Knopper {{goal|48}}
• Machlas {{goal|50||64}}
• Wamberto {{goal|72}}

|goals2 =

• Verlaat {{goal|15|o.g.}}

|stadium = Amsterdam Arena, Amsterdam

|attendance = 26,145

|referee = Željko Širić (Croatia)

|report = https://www.uefa.com/uefaeuropaleague/match/56964/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 20:00

|team1 = Dukla Banská Bystrica {{fbaicon|SVK}}

|score = 1–3

|team2 = {{fbaicon|NED}} Ajax

|goals1 =

• Malatinský {{goal|45}}

|goals2 =

• Arveladze {{goal|47}}
• Bobson {{goal|64}}
• Laudrup {{goal|90}}

|stadium = SNP Stadium, Banská Bystrica

|attendance = 4,800

|referee = José Mendes Pratas (Portugal)

|report = https://www.uefa.com/uefaeuropaleague/match/56965/

}}

Ajax won 9–2 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 21:00

|team1 = Tottenham Hotspur {{fbaicon|ENG}}

|score = 3–0

|team2 = {{fbaicon|MDA}} Zimbru Chișinău

|goals1 =

• Leonhardsen {{goal|3}}
• Perry {{goal|32}}
• Sherwood {{goal|55}}

|goals2 =

|stadium = White Hart Lane, London

|attendance = 32,660

|referee = Emanuel Zammit (Malta)

|report = https://www.uefa.com/uefaeuropaleague/match/56982/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 19:00

|team1 = Zimbru Chișinău {{fbaicon|MDA}}

|score = 0–0

|team2 = {{fbaicon|ENG}} Tottenham Hotspur

|goals1 =

|goals2 =

|stadium = Republican Stadium, Chișinău

|attendance = 4,500

|referee = Georgios Kasnaferis (Greece)

|report = https://www.uefa.com/uefaeuropaleague/match/56983/

}}

Tottenham Hotspur won 3–0 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 18:00

|team1 = Zenit Saint Petersburg {{fbaicon|RUS}}

|score = 0–3

|team2 = {{fbaicon|ITA}} Bologna

|goals1 =

|goals2 =

• Ventola {{goal|39}}
• Signori {{goal|68||90|pen.}}

|stadium = Petrovsky Stadium, Saint Petersburg

|attendance = 19,900

|referee = Kyros Vassaras (Greece)

|report = https://www.uefa.com/uefaeuropaleague/match/57034/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 17:00

|team1 = Bologna {{fbaicon|ITA}}

|score = 2–2

|team2 = {{fbaicon|RUS}} Zenit Saint Petersburg

|goals1 =

• Fontolan {{goal|39}}
• Cipriani {{goal|74}}

|goals2 =

• Panov {{goal|35}}
• Kondrashov {{goal|89}}

|stadium = Stadio Renato Dall'Ara, Bologna

|attendance = 12,126

|referee = Eric Romain (Belgium)

|report = https://www.uefa.com/uefaeuropaleague/match/57035/

}}

Bologna won 5–2 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 19:00

|team1 = Anorthosis Famagusta {{fbaicon|CYP|1960}}

|score = 1–0

|team2 = {{fbaicon|POL}} Legia Warsaw

|goals1 =

• Engomitis {{goal|83}}

|goals2 =

|stadium = Antonis Papadopoulos Stadium, Larnaca

|attendance = 3,500

|referee = Lawrence Sammut (Malta)

|report = https://www.uefa.com/uefaeuropaleague/match/57028/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 20:00

|team1 = Legia Warsaw {{fbaicon|POL}}

|score = 2–0

|team2 = {{fbaicon|CYP|1960}} Anorthosis Famagusta

|goals1 =

• Mięciel {{goal|48}}
• Czereszewski {{goal|67}}

|goals2 =

|stadium = Polish Army Stadium, Warsaw

|attendance = 4,800

|referee = Constantin Zotta (Romania)

|report = https://www.uefa.com/uefaeuropaleague/match/57029/

}}

Legia Warsaw won 2–0 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 16:00

|team1 = Locomotive Tbilisi {{fbaicon|GEO|1990}}

|score = 0–7

|team2 = {{fbaicon|GRE}} PAOK

|goals1 =

|goals2 =

• Georgiadis {{goal|16||24}}
• Sabry {{goal|43}}
• Frousos {{goal|56||63}}
• Frantzeskos {{goal|68}}
• Vryzas {{goal|69}}

|stadium = Boris Paichadze Stadium, Tbilisi

|attendance = 4,000

|referee = Attila Juhos (Hungary)

|report = https://www.uefa.com/uefaeuropaleague/match/56996/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 20:00

|team1 = PAOK {{fbaicon|GRE}}

|score = 2–0

|team2 = {{fbaicon|GEO|1990}} Locomotive Tbilisi

|goals1 =

• Valencia {{goal|53|pen.}}
• Salpingidis {{goal|81}}

|goals2 =

|stadium = Toumba Stadium, Thessaloniki

|attendance = 2,399

|referee = David Malcolm (Republic of Ireland)

|report = https://www.uefa.com/uefaeuropaleague/match/56997/

}}

PAOK won 9–0 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 20:30

|team1 = AB {{fbaicon|DEN}}

|score = 0–2

|team2 = {{fbaicon|SUI}} Grasshopper

|goals1 =

|goals2 =

• Bjur {{goal|50|o.g.}}
• Ekoku {{goal|82}}

|stadium = Gladsaxe Stadium, Gladsaxe

|attendance = 3,297

|referee = Laurent Duhamel (France)

|report = https://www.uefa.com/uefaeuropaleague/match/57012/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 20:35

|team1 = Grasshopper {{fbaicon|SUI}}

|score = 1–1

|team2 = {{fbaicon|DEN}} AB

|goals1 =

• Magro {{goal|80}}

|goals2 =

• Daugaard {{goal|31}}

|stadium = Hardturm, Zürich

|attendance = 3,800

|referee = Mika Peltola (Finland)

|report = https://www.uefa.com/uefaeuropaleague/match/57013/

}}

Grasshopper won 3–1 on aggregate.

----

{{Football box

|date = {{Start date|1999|9|16|df=y}}

|time = 20:00

|team1 = Zürich {{fbaicon|SUI}}

|score = 1–0

|team2 = {{fbaicon|BEL}} Lierse

|goals1 =

• Jamarauli {{goal|29}}

|goals2 =

|stadium = Letzigrund, Zürich

|attendance = 4,200

|referee = Michael McCurry (Scotland)

|report = https://www.uefa.com/uefaeuropaleague/match/57046/

}}

{{Football box

|date = {{Start date|1999|9|30|df=y}}

|time = 20:00

|team1 = Lierse {{fbaicon|BEL}}

|score = 3–4

|team2 = {{fbaicon|SUI}} Zürich

|goals1 =

• Van Meir {{goal|16}}
• Huysegems {{goal|72}}
• Zdebel {{goal|83}}

|goals2 =

• Jamarauli {{goal|2}}
• Frick {{goal|57}}
• Eydelie {{goal|86}}
• Daems {{goal|90|o.g.}}

|stadium = Het Lisp, Lier

|attendance = 4,936

|referee = Erol Ersoy (Turkey)

|report = https://www.uefa.com/uefaeuropaleague/match/57047/

}}

Zürich won 5–3 on aggregate.

{{reflist|group=note}}

{{reflist}}

• [https://web.archive.org/web/20111109230339/http://www.uefa.com/uefaeuropaleague/season=1999/matches/round=1276/index.html First Round Information]
• [https://www.rsssf.org/ec/ec199900.html RSSSF Page]

{{UEFA Europa League phases}}

{{1999–2000 in European football (UEFA)}}

{{DEFAULTSORT:1999-2000 UEFA Cup first round}}

Category:1999–2000 UEFA Cup

Category:UEFA Cup first rounds