1998–99 FA Premier League#Awards

{{Short description|7th season of the Premier League}}

{{EngvarB|date=April 2014}}

{{Use dmy dates|date=December 2023}}

{{Infobox football league season

| image = 1998-99 Premier League title celebrations (cropped).jpg

| pixels = 300

| competition = FA Premier League

| season = 1998–99

| dates = 15 August 1998 – 16 May 1999

| winners = Manchester United
5th Premier League title
12th English title

| relegated = Charlton Athletic
Blackburn Rovers
Nottingham Forest

| continentalcup1 = Champions League

| continentalcup1 qualifiers = Manchester United
Arsenal
Chelsea

| continentalcup2 = UEFA Cup

| continentalcup2 qualifiers = Leeds United
Newcastle United
Tottenham Hotspur

| continentalcup3 = Intertoto Cup

| continentalcup3 qualifiers = West Ham United

| league topscorer section = Top scorers

| league topscorer = Jimmy Floyd Hasselbaink
Michael Owen
Dwight Yorke
(18 goals each)

| best goalkeeper = David Seaman (19 clean sheets)

| biggest home win = {{nowrap|Liverpool 7–1 Southampton}}
(16 January 1999)
{{nowrap|Everton 6–0 West Ham United}}
(8 May 1999)

| biggest away win = {{nowrap|Nottingham Forest 1–8 Manchester United}}
(6 February 1999)

| highest scoring = {{nowrap|Nottingham Forest 1–8 Manchester United}}
(6 February 1999)

| matches = 380

| total goals = 959

| longest wins = 7 games{{cite web |url=http://www.statto.com/football/stats/england/premier-league/1998-1999/longest-sequences/full |title=English Premier League 1998–99 |publisher=statto.com |access-date=13 March 2015 |archive-url=https://web.archive.org/web/20141210095519/http://www.statto.com/football/stats/england/premier-league/1998-1999/longest-sequences/full |archive-date=10 December 2014 |url-status=dead}}
Leeds United

| longest unbeaten = 21 games
Chelsea

| longest losses = 8 games
Charlton Athletic

| longest winless = 19 games
Nottingham Forest

| highest attendance = 55,316
{{nowrap|Manchester United 2–1 Southampton}}
(27 February 1999)

| lowest attendance = 11,717
{{nowrap|Wimbledon 2–1 Coventry City}}
(5 December 1998)

| attendance = 11,623,113{{cite web |url=https://www.worldfootball.net/attendance/eng-premier-league-1998-1999/1/ |title=Premier League 1998/1999 » Attendance » Home matches |website=WorldFootball.net |date=5 January 2024 |access-date=6 January 2024 }}

| average attendance = 30,587

| prevseason = 1997–98

| nextseason = 1999–2000

}}

File:The English Premier League Winners Medal (Manchester United Museum) (262769295).jpg)]]

The 1998–99 FA Premier League (known as the FA Carling Premiership for sponsorship reasons) was the seventh season of the Premier League, the top division of English football, since its establishment in 1992. Manchester United won a treble of the league title, the FA Cup and the UEFA Champions League. They secured their fifth league title in seven seasons after outlasting Arsenal and Chelsea in a closely fought title race, losing just three league games all season.

The season was also the 100th season of top flight football in England, not counting years lost to the two World Wars. Of the original clubs in the first Football League season, only Aston Villa, Blackburn Rovers, Derby County and Everton were present for this season.

Arsenal failed to retain their title, despite having the same points tally as last season 78 points, but had at one point looked as though they were on the brink of winning the title, after beating fellow rivals Tottenham Hotspur, while Manchester United had drawn against Liverpool, 2–2. However, Manchester United pushed on and took advantage of Arsenal's 1–0 defeat at Leeds United in the penultimate match of the season and despite going 1–0 down against Tottenham on the final day, came back to win 2–1 and clinch the title. Should they have failed to win, Arsenal would have been crowned champions once more.

Chelsea, looking to build on a fourth-placed finish the previous season, were flying for much of the season and were in a good position to claim a first league title in 44 years. The Blues were second at Christmas and went top on Boxing Day. A loss at Highbury at the start of February was just a second in the league all season, and kept Chelsea in second place, just a point off the summit. Eventually, three draws in April against winnable opposition (mid-table sides Middlesbrough and Leicester City, and relegation-threatened Sheffield Wednesday) is what cost Chelsea a first Premiership crown. Had they won these, the Blues would've been champions. Chelsea had to settle for third place, earning a maiden Champions League appearance.

To achieve their success, the Manchester United playing squad had been altered substantially during the close season. A total of more than £28 million had been spent on Dwight Yorke, Jaap Stam and Jesper Blomqvist, while several older players left the club; Gary Pallister returned to Middlesbrough after nine years for £2.5 million, while Brian McClair returned to Motherwell on a free transfer. In December, however, McClair was back in the Premier League as Brian Kidd's assistant at Blackburn Rovers.

Season summary

At the end of 1998–99, the Premiership would have three Champions League places. Manchester United as well as runners-up Arsenal and third placed Chelsea would be playing in the following season's Champions League. There would only be one automatic UEFA Cup place from the league – taken by fourth-placed Leeds United. Fifth-placed West Ham United qualified for the UEFA Cup via the Intertoto Cup after achieving their highest league finish since 1986 as they continued to make progress under Harry Redknapp, outperforming several "bigger" clubs with greater resources. Also qualifying were Newcastle United via the 1998–99 FA Cup final, and Tottenham Hotspur via the League Cup.

Manchester United regained the title from Arsenal on the final day of the season, and had faced competition from Chelsea until the final stages of the season, while Aston Villa had led the table for much of the first half of the season before finishing sixth.

Bottom of the Premiership in the final table came Nottingham Forest, who suffered their third relegation in seven seasons. After winning two of their opening three matches, a club record winless run of 19 matches left them firmly rooted to the bottom. Another notable low during the season saw an 8-1 defeat at home to Manchester United, by which point Dave Bassett had been replaced by Ron Atkinson, who was unable to spark a revival in fortunes and their relegation back to the First Division was confirmed with three games remaining. Forest ultimately would not return to the top flight for another 23 years.

Second from bottom came Blackburn Rovers, who just four seasons earlier had been Premiership champions. Like Forest, a change of manager, with Roy Hodgson being replaced by Brian Kidd just before Christmas failed to have the desired outcome, a goalless draw at home to Manchester United in their penultimate game of the season sealing their fate. The final relegation place went to Charlton Athletic, who went down at the end of their first spell in the top flight for nine seasons following a 1-0 defeat at home to Sheffield Wednesday on the final day. The only newly promoted club to survive was Middlesbrough, who finished in ninth place - their highest final position for more than 20 years.

None of the teams relegated from the Premiership the previous season regained their top division status in 1999, although First Division champions Sunderland regained their Premiership place after a two-year exile. The other two relegation places went to long-term absentees from the top division. Playoff winners Watford regained their top division place after an absence of 11 years, but runners-up Bradford had been outside of the top division for 77 years. These two promotion winners surprised the observers more than any other Division One side during 1998–99, but were widely expected to struggle in the top flight.

Teams

Twenty teams competed in the league – the top seventeen teams from the previous season and the three teams promoted from the First Division. The promoted teams were Nottingham Forest, Middlesbrough (both teams sealing an immediate return to the top flight after a single season), and Charlton Athletic (playing in the top flight after an eight-year absence). This was also Charlton Athletic's first season in the Premier League. They replaced Bolton Wanderers, Barnsley and Crystal Palace, with all three relegated teams returning to the First Division after a single season in the top flight.

=Stadiums and locations=

{{location map+ |England |width=440 |float=right |caption=Locations of the 1998–99 Premier League teams |places=

{{location map~ |England |lat=51.5155|long=-0.0922|label_size=80|label=London|mark=Blue pog.svg|position=right}}

{{location map~ |England |lat=52.509103 |long=-1.884786 |label_size=80|label=Aston Villa|position=left}}

{{location map~ |England |lat=53.728569 |long=-2.489206 |label_size=80|label=Blackburn Rovers F.C.|position=left}}

{{location map~ |England |lat=52.448111 |long=-1.495611 |label_size=80|label=Coventry City F.C.|position=bottom}}

{{location map~ |England |lat=52.914911 |long=-1.447233 |label_size=80|label=Derby County F.C.|position=left}}

{{location map~ |England |lat=53.438846 |long=-2.966285 |label_size=80|label=Everton|position=left}}

{{location map~ |England |lat=53.704069 |long=-1.341731 |label_size=80|label=Leeds United F.C.|position=right}}

{{location map~ |England |lat=52.611402 |long=-1.082508 |label_size=80|label=Leicester City F.C.|position=right}}

{{location map~ |England |lat=53.430845 |long=-2.960823 |label_size=80|label=Liverpool|position=bottom}}

{{location map~ |England |lat=53.47 |long=-2.25 |label_size=80|label=Manchester United F.C.|position=right}}

{{location map~ |England |lat=54.578219 |long=-1.216822 |label_size=80|label=Middlesbrough

|position=right}}

{{location map~ |England |lat=54.974 |long=-1.614 |label_size=80|label=Newcastle United F.C.|position=left}}

{{location map~ |England |lat=52.939936 |long=-1.132886 |label_size=80|label=Nottingham Forest F.C.|position=right}}

{{location map~ |England |lat=53.370342 |long=-1.470853 |label_size=80|label=Sheffield Wednesday F.C.|position=right}}

{{location map~ |England |lat=50.905826 |long=-1.390975 |label_size=80|label=Southampton|position=left}}

{{Location map~ |England |mark=TransparentPlaceholder.png |marksize=1 |lat=55.7 |long=-0.2 |label_size=80|label=London teams:

Arsenal

Charlton Athletic

Chelsea

Tottenham Hotspur

West Ham United F.C.

Wimbledon

|position=right}}

}}

{{Location map+|Greater London

|width=300

|float=right

|caption=Greater London Premier League football clubs

|alt=Greater London Premier League football clubs

|places =

{{Location map~ |Greater London |lat=51.552 |long=-0.097 |mark=Blue pog.svg |label=Arsenal|label_size=75|marksize=|position=left}}

{{Location map~ |Greater London |lat=51.4863 |long=0.0363 |mark=Blue pog.svg |label=Charlton Athletic|label_size=75|marksize=|position=right}}

{{Location map~ |Greater London |lat=51.481667 |long=-0.191111 |mark=Blue pog.svg |label=Chelsea|label_size=75|marksize=|position=right}}

{{Location map~ |Greater London |lat=51.5974 |long=-0.0716 |mark=Blue pog.svg |label=Tottenham Hotspur F.C.|label_size=75|marksize=|position=right}}

{{Location map~ |Greater London |lat=51.531944 |long=0.039444|mark=Blue pog.svg |label=West Ham United F.C.|label_size=75|marksize=|position=right}}

{{Location map~ |Greater London |lat=51.398333 |long=-0.085556|mark=Blue pog.svg |label=Wimbledon|label_size=75|marksize=|position=bottom}}

}}

class="wikitable sortable"
Team

! Location

! Stadium

! Capacity

Arsenal

|London {{small|(Highbury)}}

|Arsenal Stadium

|align="center" | 38,419

Aston Villa

|Birmingham

|Villa Park

|align="center" | 42,573

Blackburn Rovers

|Blackburn

|Ewood Park

|align="center" | 31,367

Charlton Athletic

|London {{small|(Charlton)}}

|The Valley

|align="center" | 20,043

Chelsea

|London {{small|(Fulham)}}

|Stamford Bridge

| align="center" | 42,055

Coventry City

|Coventry

|Highfield Road

|align="center" | 23,489

Derby County

|Derby

|Pride Park Stadium

|style="text-align:center;"| 33,597

Everton

|Liverpool {{small|(Walton)}}

|Goodison Park

|align="center" | 40,569

Leeds United

|Leeds

|Elland Road

|align="center" | 40,242

Leicester City

|Leicester

|Filbert Street

|align="center" | 22,000

Liverpool

|Liverpool {{small|(Anfield)}}

|Anfield

|align="center" | 45,522

Manchester United

|Manchester

|Old Trafford

|align="center" | 68,174

Middlesbrough

| Middlesbrough

| Riverside Stadium

| align="center" | 30,000

Newcastle United

|Newcastle upon Tyne

|St James' Park

|align="center" | 52,387

Nottingham Forest

|West Bridgford

|City Ground

|align="center" | 30,445

Sheffield Wednesday

|Sheffield

|Hillsborough Stadium

|align="center" | 39,732

Southampton

|Southampton

|The Dell

|align="center" | 15,200

Tottenham Hotspur

|London {{small|(Tottenham)}}

|White Hart Lane

|align="center" | 36,240

West Ham United

|London {{small|(Upton Park)}}

|Boleyn Ground

|align="center" | 35,647

Wimbledon

|London {{small|(Selhurst)}}

|Selhurst Park{{efn|Due to Wimbledon lacking a home stadium, they played their home games at Selhurst Park, which is the home stadium of Crystal Palace.}}

|align="center" | 26,074

{{notelist}}

=Personnel and kits=

(as of 16 May 1999)

class="wikitable sortable"

! Team

! Manager

! Captain

! Kit manufacturer

! Shirt sponsor

Arsenal

|{{flagicon|FRA|1974}} Arsène Wenger

|{{flagicon|ENG}} Tony Adams

|Nike

|JVC

Aston Villa

|{{flagicon|ENG}} John Gregory

|{{flagicon|ENG}} Gareth Southgate

|Reebok

|LDV Vans

Blackburn Rovers

|{{flagicon|ENG}} Brian Kidd

|{{flagicon|ENG}} Garry Flitcroft

|Uhlsport

|CIS

Charlton Athletic

|{{flagicon|ENG}} Alan Curbishley

|{{flagicon|IRL}} Mark Kinsella

|Le Coq Sportif

|Mesh Computers

Chelsea

|{{flagicon|ITA}} Gianluca Vialli

|{{flagicon|ENG}} Dennis Wise

|Umbro

|Autoglass

Coventry City

|{{flagicon|SCO}} Gordon Strachan

|{{flagicon|SCO}} Gary McAllister

|Le Coq Sportif

|Subaru

Derby County

|{{flagicon|ENG}} Jim Smith

|{{flagicon|CRO}} Igor Štimac

|Puma

|EDS

Everton

|{{flagicon|SCO}} Walter Smith

|{{flagicon|ENG}} Dave Watson

|Umbro

|One2One

Leeds United

|{{flagicon|IRL}} David O'Leary

|{{flagicon|RSA}} Lucas Radebe

|Puma

|Packard Bell

Leicester City

|{{flagicon|NIR}} Martin O'Neill

|{{flagicon|ENG}} Steve Walsh

|Fox Leisure

|Walkers

Liverpool

|{{flagicon|FRA|1974}} Gérard Houllier

|{{flagicon|ENG}} Paul Ince

|Reebok

|Carlsberg

Manchester United

|{{flagicon|SCO}} Alex Ferguson

|{{flagicon|IRL}} Roy Keane

|Umbro

|Sharp

Middlesbrough

|{{flagicon|ENG}} Bryan Robson

|{{flagicon|IRL}} Andy Townsend

|Erreà

|Cellnet

Newcastle United

|{{flagicon|NED}} Ruud Gullit

|{{flagicon|ENG}} Alan Shearer

|Adidas

|Newcastle Brown Ale

Nottingham Forest

|{{flagicon|ENG}} Ron Atkinson

|{{flagicon|ENG}} Steve Chettle

|Umbro

|Pinnacle Insurance

Sheffield Wednesday

|{{flagicon|ENG}} Danny Wilson

|{{flagicon|ENG}} Peter Atherton

|Puma

|Sanderson

Southampton

|{{flagicon|ENG}} Dave Jones

|{{flagicon|ENG}} Matt Le Tissier

|Pony

|Sanderson

Tottenham Hotspur

|{{flagicon|SCO}} George Graham

|{{flagicon|ENG}} Sol Campbell

|Pony

|Hewlett-Packard

West Ham United

|{{flagicon|ENG}} Harry Redknapp

|{{flagicon|NIR}} Steve Lomas

|Pony

|Dr. Martens

Wimbledon

|{{flagicon|ENG}} Terry Burton
{{flagicon|ENG}} Mick Harford (caretaker)

|{{flagicon|JAM}} Robbie Earle

|Lotto

|Elonex

=Managerial changes=

class="wikitable"
Team

! Outgoing manager

! Manner of departure

! Date of vacancy

! Position in table

! Incoming manager

! Date of appointment

Sheffield Wednesday

| {{flagicon|ENG}} Ron Atkinson

| End of caretaker spell

| 17 May 1998

|rowspan=3| Pre-season

| {{flagicon|ENG}} Danny Wilson

| 6 July 1998

Everton

| {{flagicon|ENG}} Howard Kendall

| Resigned

|rowspan=2| 1 July 1998

| {{flagicon|SCO}} Walter Smith

|rowspan=2| 1 July 1998

Liverpool

| {{flagicon|ENG}} Roy Evans (sole charge)

| N/A{{efn|Houllier joined Evans as co-manager}}

| {{flagicon|ENG}} Roy Evans
{{flagicon|FRA|1974}} Gérard Houllier (co-managers)

Newcastle United

| {{flagicon|SCO}} Kenny Dalglish

|rowspan=2| Sacked

| 27 August 1998

| 13th

| {{flagicon|NED}} Ruud Gullit

| 27 August 1998

rowspan=2| Tottenham Hotspur

| {{flagicon|SUI}} Christian Gross

| 5 September 1998

| 14th

| {{flagicon|ENG}} David Pleat
{{flagicon|IRL}} Chris Hughton (co-caretakers)

| 7 September 1998

{{flagicon|ENG}} David Pleat
{{flagicon|IRL}} Chris Hughton

| End of caretaker spell

|rowspan=2| 1 October 1998

| 13th

| {{flagicon|SCO}} George Graham

|rowspan=2| 1 October 1998

Leeds United

| {{flagicon|SCO}} George Graham

| Signed by Tottenham

| 7th

| {{flagicon|IRL}} David O'Leary

Liverpool

| {{flagicon|ENG}} Roy Evans (as co-manager)

| Resigned

| 12 November 1998

| 11th

| {{flagicon|FRA|1974}} Gérard Houllier (taking sole charge)

| 12 November 1998

rowspan=2| Blackburn Rovers

| {{flagicon|ENG}} Roy Hodgson

| Sacked

| 21 November 1998

|rowspan=3| 20th

| {{flagicon|ENG}} Tony Parkes (caretaker)

| 21 November 1998

{{flagicon|ENG}} Tony Parkes

| End of caretaker spell

| 4 December 1998

| {{flagicon|ENG}} Brian Kidd

| 4 December 1998

Nottingham Forest

| {{flagicon|ENG}} Dave Bassett

| Sacked

| 5 January 1999

| {{flagicon|ENG}} Ron Atkinson (caretaker)

| 5 January 1999

Wimbledon

| {{flagicon|IRE}} Joe Kinnear

| Illness

| 3 March 1999{{efn|Kinnear remained contracted as manager until the season ended, and did not return to the club}}

| 6th

|{{flagicon|ENG}} Terry Burton
{{flagicon|ENG}} Mick Harford (co-caretakers)

| 3 March 1999

{{notelist}}

League table

{{#invoke:sports table|main|style=WDL

|res_col_header=QR

|show_limit=5

|team1=MUN|name_MUN=Manchester United

|team2=ARS|name_ARS=Arsenal

|team3=CHE|name_CHE=Chelsea

|team4=LEE|name_LEE=Leeds United

|team5=WHU|name_WHU=West Ham United

|team6=AST|name_AST=Aston Villa

|team7=LIV|name_LIV=Liverpool

|team8=DER|name_DER=Derby County

|team9=MID|name_MID=Middlesbrough

|team10=LEI|name_LEI=Leicester City

|team11=TOT|name_TOT=Tottenham Hotspur

|team12=SHW|name_SHW=Sheffield Wednesday

|team13=NEW|name_NEW=Newcastle United

|team14=EVE|name_EVE=Everton

|team15=COV|name_COV=Coventry City

|team16=WDN|name_WDN=Wimbledon

|team17=SOU|name_SOU=Southampton

|team18=CHA|name_CHA=Charlton Athletic

|team19=BLB|name_BLB=Blackburn Rovers

|team20=NOT|name_NOT=Nottingham Forest

|win_MUN=22|draw_MUN=13|loss_MUN=3|gf_MUN=80|ga_MUN=37|status_MUN=C

|win_ARS=22|draw_ARS=12|loss_ARS=4|gf_ARS=59|ga_ARS=17

|win_CHE=20|draw_CHE=15|loss_CHE=3|gf_CHE=57|ga_CHE=30

|win_LEE=18|draw_LEE=13|loss_LEE=7|gf_LEE=62|ga_LEE=34

|win_WHU=16|draw_WHU=9|loss_WHU=13|gf_WHU=46|ga_WHU=53

|win_AST=15|draw_AST=10|loss_AST=13|gf_AST=51|ga_AST=46

|win_LIV=15|draw_LIV=9|loss_LIV=14|gf_LIV=68|ga_LIV=49

|win_DER=13|draw_DER=13|loss_DER=12|gf_DER=40|ga_DER=45

|win_MID=12|draw_MID=15|loss_MID=11|gf_MID=48|ga_MID=54

|win_LEI=12|draw_LEI=13|loss_LEI=13|gf_LEI=40|ga_LEI=46

|win_TOT=11|draw_TOT=14|loss_TOT=13|gf_TOT=47|ga_TOT=50

|win_SHW=13|draw_SHW=7|loss_SHW=18|gf_SHW=41|ga_SHW=42

|win_NEW=11|draw_NEW=13|loss_NEW=14|gf_NEW=48|ga_NEW=54

|win_EVE=11|draw_EVE=10|loss_EVE=17|gf_EVE=42|ga_EVE=47

|win_COV=11|draw_COV=9|loss_COV=18|gf_COV=39|ga_COV=51

|win_WDN=10|draw_WDN=12|loss_WDN=16|gf_WDN=40|ga_WDN=63

|win_SOU=11|draw_SOU=8|loss_SOU=19|gf_SOU=37|ga_SOU=64

|win_CHA=8|draw_CHA=12|loss_CHA=18|gf_CHA=41|ga_CHA=56|status_CHA=R

|win_BLB=7|draw_BLB=14|loss_BLB=17|gf_BLB=38|ga_BLB=52|status_BLB=R

|win_NOT=7|draw_NOT=9|loss_NOT=22|gf_NOT=35|ga_NOT=69|status_NOT=R

|col_CLGS=green1|text_CLGS=Qualification for the Champions League first group stage

|result1=CLGS|result2=CLGS

|col_CL3=green2|text_CL3=Qualification for the Champions League third qualifying round

|result3=CL3

|col_UC1=blue1|text_UC1=Qualification for the UEFA Cup first round

|result4=UC1

|col_IC3=#CCCCFF|text_IC3=Qualification for the Intertoto Cup third round

|result5=IC3

|col_TOT=blue1|text_TOT=Qualification for the UEFA Cup first round

|note_res_TOT=Tottenham Hotspur qualified for the UEFA Cup as League Cup winners.

|result11=TOT

|col_NEW=blue1|text_NEW=Qualification for the UEFA Cup first round

|note_res_NEW=As Manchester United qualified for the Champions League, their UEFA Cup place as FA Cup winners defaulted to Newcastle United, the runners-up.

|result13=NEW

|col_R=red1|text_R=Relegation to Football League First Division

|result18=R|result19=R|result20=R

|class_rules=1) points; 2) goal difference; 3) number of goals scored.

|update=complete

|source=[https://www.premierleague.com/tables?co=1&se=7&ha=-1 Premier League]

}}

Results

{{#invoke:Sports results|main

|matches_style=FBR|solid_cell=grey

|team1=ARS|team2=AVL|team3=BLB|team4=CHA|team5=CHE

|team6=COV|team7=DER|team8=EVE|team9=LEE|team10=LEI

|team11=LIV|team12=MUN|team13=MID|team14=NEW|team15=NFO

|team16=SHW|team17=SOU|team18=TOT|team19=WHU|team20=WIM

|name_ARS=Arsenal

|match_ARS_AVL=1–0

|match_ARS_BLB=1–0

|match_ARS_CHA=0–0

|match_ARS_CHE=1–0

|match_ARS_COV=2–0

|match_ARS_DER=1–0

|match_ARS_EVE=1–0

|match_ARS_LEE=3–1

|match_ARS_LEI=5–0

|match_ARS_LIV=0–0

|match_ARS_MUN=3–0

|match_ARS_MID=1–1

|match_ARS_NEW=3–0

|match_ARS_NFO=2–1

|match_ARS_SHW=3–0

|match_ARS_SOU=1–1

|match_ARS_TOT=0–0

|match_ARS_WHU=1–0

|match_ARS_WIM=5–1

|name_AVL=Aston Villa

|match_AVL_ARS=3–2

|match_AVL_BLB=1–3

|match_AVL_CHA=3–4

|match_AVL_CHE=0–3

|match_AVL_COV=1–4

|match_AVL_DER=1–0

|match_AVL_EVE=3–0

|match_AVL_LEE=1–2

|match_AVL_LEI=1–1

|match_AVL_LIV=2–4

|match_AVL_MUN=1–1

|match_AVL_MID=3–1

|match_AVL_NEW=1–0

|match_AVL_NFO=2–0

|match_AVL_SHW=2–1

|match_AVL_SOU=3–0

|match_AVL_TOT=3–2

|match_AVL_WHU=0–0

|match_AVL_WIM=2–0

|name_BLB=Blackburn Rovers

|match_BLB_ARS=1–2

|match_BLB_AVL=2–1

|match_BLB_CHA=1–0

|match_BLB_CHE=3–4

|match_BLB_COV=1–2

|match_BLB_DER=0–0

|match_BLB_EVE=1–2

|match_BLB_LEE=1–0

|match_BLB_LEI=1–0

|match_BLB_LIV=1–3

|match_BLB_MUN=0–0

|match_BLB_MID=0–0

|match_BLB_NEW=0–0

|match_BLB_NFO=1–2

|match_BLB_SHW=1–4

|match_BLB_SOU=0–2

|match_BLB_TOT=1–1

|match_BLB_WHU=3–0

|match_BLB_WIM=3–1

|name_CHA=Charlton Athletic

|match_CHA_ARS=0–1

|match_CHA_AVL=0–1

|match_CHA_BLB=0–0

|match_CHA_CHE=0–1

|match_CHA_COV=1–1

|match_CHA_DER=1–2

|match_CHA_EVE=1–2

|match_CHA_LEE=1–1

|match_CHA_LEI=0–0

|match_CHA_LIV=1–0

|match_CHA_MUN=0–1

|match_CHA_MID=1–1

|match_CHA_NEW=2–2

|match_CHA_NFO=0–0

|match_CHA_SHW=0–1

|match_CHA_SOU=5–0

|match_CHA_TOT=1–4

|match_CHA_WHU=4–2

|match_CHA_WIM=2–0

|name_CHE=Chelsea

|match_CHE_ARS=0–0

|match_CHE_AVL=2–1

|match_CHE_BLB=1–1

|match_CHE_CHA=2–1

|match_CHE_COV=2–1

|match_CHE_DER=2–1

|match_CHE_EVE=3–1

|match_CHE_LEE=1–0

|match_CHE_LEI=2–2

|match_CHE_LIV=2–1

|match_CHE_MUN=0–0

|match_CHE_MID=2–0

|match_CHE_NEW=1–1

|match_CHE_NFO=2–1

|match_CHE_SHW=1–1

|match_CHE_SOU=1–0

|match_CHE_TOT=2–0

|match_CHE_WHU=0–1

|match_CHE_WIM=3–0

|name_COV=Coventry City

|match_COV_ARS=0–1

|match_COV_AVL=1–2

|match_COV_BLB=1–1

|match_COV_CHA=2–1

|match_COV_CHE=2–1

|match_COV_DER=1–1

|match_COV_EVE=3–0

|match_COV_LEE=2–2

|match_COV_LEI=1–1

|match_COV_LIV=2–1

|match_COV_MUN=0–1

|match_COV_MID=1–2

|match_COV_NEW=1–5

|match_COV_NFO=4–0

|match_COV_SHW=1–0

|match_COV_SOU=1–0

|match_COV_TOT=1–1

|match_COV_WHU=0–0

|match_COV_WIM=2–1

|name_DER=Derby County

|match_DER_ARS=0–0

|match_DER_AVL=2–1

|match_DER_BLB=1–0

|match_DER_CHA=0–2

|match_DER_CHE=2–2

|match_DER_COV=0–0

|match_DER_EVE=2–1

|match_DER_LEE=2–2

|match_DER_LEI=2–0

|match_DER_LIV=3–2

|match_DER_MUN=1–1

|match_DER_MID=2–1

|match_DER_NEW=3–4

|match_DER_NFO=1–0

|match_DER_SHW=1–0

|match_DER_SOU=0–0

|match_DER_TOT=0–1

|match_DER_WHU=0–2

|match_DER_WIM=0–0

|name_EVE=Everton

|match_EVE_ARS=0–2

|match_EVE_AVL=0–0

|match_EVE_BLB=0–0

|match_EVE_CHA=4–1

|match_EVE_CHE=0–0

|match_EVE_COV=2–0

|match_EVE_DER=0–0

|match_EVE_LEE=0–0

|match_EVE_LEI=0–0

|match_EVE_LIV=0–0

|match_EVE_MUN=1–4

|match_EVE_MID=5–0

|match_EVE_NEW=1–0

|match_EVE_NFO=0–1

|match_EVE_SHW=1–2

|match_EVE_SOU=1–0

|match_EVE_TOT=0–1

|match_EVE_WHU=6–0

|match_EVE_WIM=1–1

|name_LEE=Leeds United

|match_LEE_ARS=1–0

|match_LEE_AVL=0–0

|match_LEE_BLB=1–0

|match_LEE_CHA=4–1

|match_LEE_CHE=0–0

|match_LEE_COV=2–0

|match_LEE_DER=4–1

|match_LEE_EVE=1–0

|match_LEE_LEI=0–1

|match_LEE_LIV=0–0

|match_LEE_MUN=1–1

|match_LEE_MID=2–0

|match_LEE_NEW=0–1

|match_LEE_NFO=3–1

|match_LEE_SHW=2–1

|match_LEE_SOU=3–0

|match_LEE_TOT=2–0

|match_LEE_WHU=4–0

|match_LEE_WIM=2–2

|name_LEI=Leicester City

|match_LEI_ARS=1–1

|match_LEI_AVL=2–2

|match_LEI_BLB=1–1

|match_LEI_CHA=1–1

|match_LEI_CHE=2–4

|match_LEI_COV=1–0

|match_LEI_DER=1–2

|match_LEI_EVE=2–0

|match_LEI_LEE=1–2

|match_LEI_LIV=1–0

|match_LEI_MUN=2–6

|match_LEI_MID=0–1

|match_LEI_NEW=2–0

|match_LEI_NFO=3–1

|match_LEI_SHW=0–2

|match_LEI_SOU=2–0

|match_LEI_TOT=2–1

|match_LEI_WHU=0–0

|match_LEI_WIM=1–1

|name_LIV=Liverpool

|match_LIV_ARS=0–0

|match_LIV_AVL=0–1

|match_LIV_BLB=2–0

|match_LIV_CHA=3–3

|match_LIV_CHE=1–1

|match_LIV_COV=2–0

|match_LIV_DER=1–2

|match_LIV_EVE=3–2

|match_LIV_LEE=1–3

|match_LIV_LEI=0–1

|match_LIV_MUN=2–2

|match_LIV_MID=3–1

|match_LIV_NEW=4–2

|match_LIV_NFO=5–1

|match_LIV_SHW=2–0

|match_LIV_SOU=7–1

|match_LIV_TOT=3–2

|match_LIV_WHU=2–2

|match_LIV_WIM=3–0

|name_MUN=Manchester United

|match_MUN_ARS=1–1

|match_MUN_AVL=2–1

|match_MUN_BLB=3–2

|match_MUN_CHA=4–1

|match_MUN_CHE=1–1

|match_MUN_COV=2–0

|match_MUN_DER=1–0

|match_MUN_EVE=3–1

|match_MUN_LEE=3–2

|match_MUN_LEI=2–2

|match_MUN_LIV=2–0

|match_MUN_MID=2–3

|match_MUN_NEW=0–0

|match_MUN_NFO=3–0

|match_MUN_SHW=3–0

|match_MUN_SOU=2–1

|match_MUN_TOT=2–1

|match_MUN_WHU=4–1

|match_MUN_WIM=5–1

|name_MID=Middlesbrough

|match_MID_ARS=1–6

|match_MID_AVL=0–0

|match_MID_BLB=2–1

|match_MID_CHA=2–0

|match_MID_CHE=0–0

|match_MID_COV=2–0

|match_MID_DER=1–1

|match_MID_EVE=2–2

|match_MID_LEE=0–0

|match_MID_LEI=0–0

|match_MID_LIV=1–3

|match_MID_MUN=0–1

|match_MID_NEW=2–2

|match_MID_NFO=1–1

|match_MID_SHW=4–0

|match_MID_SOU=3–0

|match_MID_TOT=0–0

|match_MID_WHU=1–0

|match_MID_WIM=3–1

|name_NEW=Newcastle United

|match_NEW_ARS=1–1

|match_NEW_AVL=2–1

|match_NEW_BLB=1–1

|match_NEW_CHA=0–0

|match_NEW_CHE=0–1

|match_NEW_COV=4–1

|match_NEW_DER=2–1

|match_NEW_EVE=1–3

|match_NEW_LEE=0–3

|match_NEW_LEI=1–0

|match_NEW_LIV=1–4

|match_NEW_MUN=1–2

|match_NEW_MID=1–1

|match_NEW_NFO=2–0

|match_NEW_SHW=1–1

|match_NEW_SOU=4–0

|match_NEW_TOT=1–1

|match_NEW_WHU=0–3

|match_NEW_WIM=3–1

|name_NFO=Nottingham Forest

|match_NFO_ARS=0–1

|match_NFO_AVL=2–2

|match_NFO_BLB=2–2

|match_NFO_CHA=0–1

|match_NFO_CHE=1–3

|match_NFO_COV=1–0

|match_NFO_DER=2–2

|match_NFO_EVE=0–2

|match_NFO_LEE=1–1

|match_NFO_LEI=1–0

|match_NFO_LIV=2–2

|match_NFO_MUN=1–8

|match_NFO_MID=1–2

|match_NFO_NEW=1–2

|match_NFO_SHW=2–0

|match_NFO_SOU=1–1

|match_NFO_TOT=0–1

|match_NFO_WHU=0–0

|match_NFO_WIM=0–1

|name_SHW=Sheffield Wednesday

|match_SHW_ARS=1–0

|match_SHW_AVL=0–1

|match_SHW_BLB=3–0

|match_SHW_CHA=3–0

|match_SHW_CHE=0–0

|match_SHW_COV=1–2

|match_SHW_DER=0–1

|match_SHW_EVE=0–0

|match_SHW_LEE=0–2

|match_SHW_LEI=0–1

|match_SHW_LIV=1–0

|match_SHW_MUN=3–1

|match_SHW_MID=3–1

|match_SHW_NEW=1–1

|match_SHW_NFO=3–2

|match_SHW_SOU=0–0

|match_SHW_TOT=0–0

|match_SHW_WHU=0–1

|match_SHW_WIM=1–2

|name_SOU=Southampton

|match_SOU_ARS=0–0

|match_SOU_AVL=1–4

|match_SOU_BLB=3–3

|match_SOU_CHA=3–1

|match_SOU_CHE=0–2

|match_SOU_COV=2–1

|match_SOU_DER=0–1

|match_SOU_EVE=2–0

|match_SOU_LEE=3–0

|match_SOU_LEI=2–1

|match_SOU_LIV=1–2

|match_SOU_MUN=0–3

|match_SOU_MID=3–3

|match_SOU_NEW=2–1

|match_SOU_NFO=1–2

|match_SOU_SHW=1–0

|match_SOU_TOT=1–1

|match_SOU_WHU=1–0

|match_SOU_WIM=3–1

|name_TOT=Tottenham Hotspur

|match_TOT_ARS=1–3

|match_TOT_AVL=1–0

|match_TOT_BLB=2–1

|match_TOT_CHA=2–2

|match_TOT_CHE=2–2

|match_TOT_COV=0–0

|match_TOT_DER=1–1

|match_TOT_EVE=4–1

|match_TOT_LEE=3–3

|match_TOT_LEI=0–2

|match_TOT_LIV=2–1

|match_TOT_MUN=2–2

|match_TOT_MID=0–3

|match_TOT_NEW=2–0

|match_TOT_NFO=2–0

|match_TOT_SHW=0–3

|match_TOT_SOU=3–0

|match_TOT_WHU=1–2

|match_TOT_WIM=0–0

|name_WHU=West Ham United

|match_WHU_ARS=0–4

|match_WHU_AVL=0–0

|match_WHU_BLB=2–0

|match_WHU_CHA=0–1

|match_WHU_CHE=1–1

|match_WHU_COV=2–0

|match_WHU_DER=5–1

|match_WHU_EVE=2–1

|match_WHU_LEE=1–5

|match_WHU_LEI=3–2

|match_WHU_LIV=2–1

|match_WHU_MUN=0–0

|match_WHU_MID=4–0

|match_WHU_NEW=2–0

|match_WHU_NFO=2–1

|match_WHU_SHW=0–4

|match_WHU_SOU=1–0

|match_WHU_TOT=2–1

|match_WHU_WIM=3–4

|name_WIM=Wimbledon

|match_WIM_ARS=1–0

|match_WIM_AVL=0–0

|match_WIM_BLB=1–1

|match_WIM_CHA=2–1

|match_WIM_CHE=1–2

|match_WIM_COV=2–1

|match_WIM_DER=2–1

|match_WIM_EVE=1–2

|match_WIM_LEE=1–1

|match_WIM_LEI=0–1

|match_WIM_LIV=1–0

|match_WIM_MUN=1–1

|match_WIM_MID=2–2

|match_WIM_NEW=1–1

|match_WIM_NFO=1–3

|match_WIM_SHW=2–1

|match_WIM_SOU=0–2

|match_WIM_TOT=3–1

|match_WIM_WHU=0–0

|update=complete

|source=[https://archive.today/20230101140814/https://www.11v11.com/competitions/premier-league/1999/matches/ 11v11]

}}

Season statistics

=Scoring=

==Top scorers==

File:欧文 (2013).jpg was the joint top scorer for the second time, with 18 goals.]]

class="wikitable"
Rank

!Player

!Club

!Goals

rowspan=3 align=center|1

|{{flagicon|NLD}} Jimmy Floyd Hasselbaink

|Leeds United

|rowspan=3 align=center|18

{{flagicon|ENG}} Michael Owen

|Liverpool

{{flagicon|TTO}} Dwight Yorke

|Manchester United

rowspan=2 align=center|4

|{{flagicon|FRA|1974}} Nicolas Anelka

|Arsenal

|rowspan=2 align=center|17

{{flagicon|ENG}} Andy Cole

|Manchester United

align=center|6

|{{flagicon|COL}} Hámilton Ricard

|Middlesbrough

|align=center|15

rowspan=4 align=center|7

|{{flagicon|ENG}} Dion Dublin

|Aston Villa

|rowspan=4 align=center|14

{{flagicon|ENG}} Robbie Fowler

|Liverpool

{{flagicon|ENG}} Julian Joachim

|Aston Villa

{{flagicon|ENG}} Alan Shearer

|Newcastle United

== Hat-tricks ==

{{main|List of Premier League hat-tricks}}

File:Solskjaer cropped.jpg became the first player to score a hat-trick as a substitute in the Premier League.]]

class="wikitable"
PlayerForAgainststyle="text-align:center"| ResultDateRef
{{flagicon|ENG}} {{sortname|Clive|Mendonca}}Charlton AthleticSouthampton5–0 (H){{dts|format=dmy|1998|8|22}}{{cite news |url=https://www.independent.co.uk/sport/football-roundup--mendoncas-valley-high-1173529.html |archive-url=https://ghostarchive.org/archive/20220501/https://www.independent.co.uk/sport/football-roundup--mendoncas-valley-high-1173529.html |archive-date=1 May 2022 |url-access=subscription |url-status=live |work=The Independent |access-date=15 July 2009 |date=22 August 1998|title=Football Round-up: Mendonca's Valley high |first=Geoff |last=Brown |location=London}}{{cbignore}}
{{flagicon|ENG}} {{sortname|Michael|Owen}}LiverpoolNewcastle United4–1 (A){{dts|format=dmy|1998|8|30}}{{cite news |url=https://www.independent.co.uk/sport/football-owen-defines-gullits-task-with-hattrick-1175303.html |archive-url=https://ghostarchive.org/archive/20220501/https://www.independent.co.uk/sport/football-owen-defines-gullits-task-with-hattrick-1175303.html |archive-date=1 May 2022 |url-access=subscription |url-status=live |work=The Independent |title=Football: Owen defines Gullit's task with hat-trick|first=Glenn |last=Moore |date=31 August 1998 |access-date=15 July 2009 |location=London}}{{cbignore}}
{{flagicon|ENG}} {{sortname|Michael|Owen}}4LiverpoolNottingham Forest5–1 (H){{dts|format=dmy|1998|10|24}}{{cite news |url=https://www.nytimes.com/1998/10/25/sports/plus-soccer-england-owen-returns-with-four-goals.html |work=The New York Times |title=Soccer – England: Owen Returns With Four Goals|access-date=15 July 2009 |date=26 October 1998}}
{{flagicon|ENG}} {{sortname|Dion|Dublin}}Aston VillaLeicester City4–1 (A){{dts|format=dmy|1998|11|14}}{{cite news |url=https://www.independent.co.uk/sport/football-dublins-treble-leaves-villa-in-clover-1185003.html |archive-url=https://ghostarchive.org/archive/20220501/https://www.independent.co.uk/sport/football-dublins-treble-leaves-villa-in-clover-1185003.html |archive-date=1 May 2022 |url-access=subscription |work=The Independent |first=Norman |last=Fox |date=15 November 1998 |access-date=18 July 2009 |title=Football: Dublin's treble leaves Villa in clover |location=London}}{{cbignore}}
{{flagicon|ENG}} {{sortname|Robbie|Fowler}}LiverpoolAston Villa4–2 (A){{dts|format=dmy|1998|11|21}}{{cite news |url=https://www.independent.co.uk/sport/football-fowlers-trick-trumps-villa-1186463.html |archive-url=https://ghostarchive.org/archive/20220501/https://www.independent.co.uk/sport/football-fowlers-trick-trumps-villa-1186463.html |archive-date=1 May 2022 |url-access=subscription |url-status=live |work=The Independent |title=Football Fowler trick trumps Villa |access-date=15 July 2009 |date=22 November 1998|first=Nick |last=Townsend |location=London}}{{cbignore}}
{{flagicon|ENG}} {{sortname|Chris|Armstrong|Chris Armstrong (footballer, born 1971)}}Tottenham HotspurEverton4–1 (H){{dts|format=dmy|1998|12|28}}{{cite news |url=https://www.independent.co.uk/sport/football-armstrong-treble-traumatises-everton-1194826.html |archive-url=https://ghostarchive.org/archive/20220501/https://www.independent.co.uk/sport/football-armstrong-treble-traumatises-everton-1194826.html |archive-date=1 May 2022 |url-access=subscription |url-status=live |work=The Independent |access-date=15 July 2009 |date=29 December 1998|title=Football: Armstrong treble traumatises Everton|first=Mike |last=Rowbottom |location=London}}{{cbignore}}
{{flagicon|ENG}} {{sortname|Darren|Huckerby}}Coventry CityNottingham Forest4–0 (H){{dts|format=dmy|1999|1|9}}{{cite news |url=https://www.theguardian.com/football/1999/jan/09/match.sport1|title=Huckerby hat-trick fells forlorn Forest |date=9 January 1999|access-date=16 July 2009 |first=Duncan |last=Mackay |work=The Guardian |location=London}}
{{flagicon|ENG}} {{sortname|Robbie|Fowler}}PLiverpoolSouthampton7–1 (H){{dts|format=dmy|1999|1|16}}{{cite news |url=https://www.independent.co.uk/sport/football-fowler-preys-on-sorry-saints-1074398.html |archive-url=https://ghostarchive.org/archive/20220501/https://www.independent.co.uk/sport/football-fowler-preys-on-sorry-saints-1074398.html |archive-date=1 May 2022 |url-access=subscription |url-status=live |title=Football: Fowler preys on sorry Saints |access-date=16 July 2009 |date=17 January 1999|first=Neil |last=Bramwell|work=The Independent |location=London}}{{cbignore}}
{{flagicon|TRI}} {{sortname|Dwight|Yorke}}Manchester UnitedLeicester City6–2 (A){{dts|format=dmy|1999|1|16}}{{Cite web |url=http://www.sportinglife.com/football/cc_championship/leicester/reports/story_get.cgi?STORY_NAME=soccer/99/01/16/SOCCER_Leicester_Nightlead.html&TEAMHD=leicester&DIV=nat1&TEAM=LEICESTER--CITY&RH=Leicester--City&PREV_SEASON=1997 |publisher=Sporting Life |access-date=15 July 2009 |title=Leicester 2–6 Manchester United |first=John |last=Curtis |archive-date=5 June 2011 |archive-url=https://web.archive.org/web/20110605030220/http://www.sportinglife.com/football/cc_championship/leicester/reports/story_get.cgi?STORY_NAME=soccer%2F99%2F01%2F16%2FSOCCER_Leicester_Nightlead.html&TEAMHD=leicester&DIV=nat1&TEAM=LEICESTER--CITY&RH=Leicester--City&PREV_SEASON=1997 |url-status=dead }}
{{flagicon|NOR}} {{sortname|Ole Gunnar|Solskjær}}4 {{dagger}}Manchester UnitedNottingham Forest8–1 (A){{dts|format=dmy|1999|2|6}}{{cite news |url=http://news.bbc.co.uk/2/hi/sport/football/fa_carling_premiership/273755.stm |title=United romp to record win |access-date=17 September 2017 |date=7 February 1999| work=BBC News}}
{{flagicon|FRA|1974}} {{sortname|Nicolas|Anelka}}ArsenalLeicester City5–0 (H){{dts|format=dmy|1999|2|20}}{{cite news |url=https://www.independent.co.uk/sport/football-arsenal-fired-by-anelka-hattrick-1072158.html |archive-url=https://ghostarchive.org/archive/20220501/https://www.independent.co.uk/sport/football-arsenal-fired-by-anelka-hattrick-1072158.html |archive-date=1 May 2022 |url-access=subscription |url-status=live |title=Football: Arsenal fired by Anelka hat-trick |access-date=16 July 2009 |date=21 February 1999|first=Nick|last=Townsend |work=The Independent |location=London}}{{cbignore}}
{{flagicon|ENG}} {{sortname|Kevin|Campbell|Kevin Campbell (footballer)}}EvertonWest Ham United6–0 (H){{dts|format=dmy|1999|5|8}}{{cite news |url=http://www.toffeeweb.com/season/98-99/reports/west-ham_h.htm#ST |title=Everton joy as Campbell serves up treble treat |work=The Sunday Times |first=Louise |last=Taylor |date=9 May 1999 |access-date=13 July 2009}}

:Note: 4 Player scored 4 goals; P Player scored a perfect hat-trick; {{dagger}} Player scored hat-trick as a substitute; (H) – Home; (A) – Away

==Top assists==

File:Dennis Bergkamp.jpg was the joint top assist provider with 13 goals for the club in the 1998–99 Premier League season.]]

class="wikitable" style="text-align:center"

! Rank

! Player

! Club

! Assists{{cite web |url=https://www.premierleague.com/stats/top/players/goal_assist |title=Statistical Leaders – 1999 |publisher=Premier League |access-date=5 May 2018 |url-status=live |archive-url=https://web.archive.org/web/20170624144700/https://www.premierleague.com/stats/top/players/goal_assist |archive-date=24 June 2017}}

rowspan="2" | 1

| align="left" | {{flagicon|NED}} Dennis Bergkamp

| align="left" | Arsenal

| rowspan="2" | 13

align="left" | {{flagicon|NED}} Jimmy Floyd Hasselbaink

| align="left" | Leeds United

rowspan="4" | 3

| align="left" | {{flagicon|ENG}} David Beckham

| align="left" | Manchester United

| rowspan="4" | 11

align="left" | {{flagicon|ISR}} Eyal Berkovic

| align="left" | West Ham United

align="left" | {{flagicon|ENG}} Steve Guppy

| align="left" | Leicester City

align="left" | {{flagicon|TRI}} Dwight Yorke

| align="left" | Manchester United

7

| align="left" | {{flagicon|FRA|1974}} David Ginola

| align="left" | Tottenham Hotspur

| 10

rowspan="2" | 8

| align="left" | {{flagicon|ENG}} Darren Anderton

| align="left" | Tottenham Hotspur

| rowspan="2" | 9

align="left" | {{flagicon|AUS}} Harry Kewell

| align="left" | Leeds United

10

| align="left" | {{flagicon|ENG}} James Beattie

| align="left" | Southampton

| 7

Awards

=Monthly awards=

class="wikitable"
rowspan="2"|Month

!colspan="2"|Manager of the Month

!colspan="2"|Player of the Month

Manager

!Club

!Player

!Club

August

|{{flagicon|ENG}} Alan Curbishley

|Charlton Athletic

|{{flagicon|ENG}} Michael Owen

|Liverpool

September

|{{flagicon|ENG}} John Gregory

|Aston Villa

|{{flagicon|ENG}} Alan Shearer

|Newcastle United

October

|{{flagicon|NIR}} Martin O'Neill

|Leicester City

|{{flagicon|IRE}} Roy Keane

|Manchester United

November

|{{flagicon|ENG}} Harry Redknapp

|West Ham United

|{{flagicon|ENG}} Dion Dublin

|Aston Villa

December

|{{flagicon|ENG}} Brian Kidd

|Blackburn Rovers{{cite news |url=https://www.theguardian.com/football/1999/feb/05/newsstory.sport13 |title=Kidd's silent runnings |first=Roy |last=Collins |newspaper=The Guardian |location=London |date=5 February 1999 |access-date=12 September 2018}}

|{{flagicon|FRA|1974}} David Ginola

|Tottenham Hotspur

January

|{{flagicon|SCO}} Alex Ferguson

|Manchester United

|{{flagicon|TRI}} Dwight Yorke

|Manchester United

February

|{{flagicon|ENG}} Alan Curbishley

|Charlton Athletic

|{{flagicon|FRA|1974}} Nicolas Anelka

|Arsenal

March

|{{flagicon|IRE}} David O'Leary

|Leeds United

|{{flagicon|ENG}} Ray Parlour

|Arsenal

April

|{{flagicon|SCO}} Alex Ferguson

|Manchester United

|{{flagicon|ENG}} Kevin Campbell

|Everton

=Annual awards=

class="wikitable"
Award

! Winner

! Club

Premier League Manager of the Season

| {{flagicon|SCO}} Alex Ferguson

| Manchester United

Premier League Player of the Season

| {{flagicon|TRI}} Dwight Yorke

| Manchester United

PFA Players' Player of the Year

| {{flagicon|FRA|1974}} David Ginola

| Tottenham Hotspur

PFA Young Player of the Year

| {{flagicon|FRA|1974}} Nicolas Anelka

| Arsenal

FWA Footballer of the Year

| {{flagicon|FRA|1974}} David Ginola

| Tottenham Hotspur

class="wikitable" style="text-align:center"
colspan="13" | PFA Team of the Year
Goalkeeper

|colspan="12"| {{flagicon|ENG}} Nigel Martyn (Leeds United)

Defenders

|colspan="3"| {{flagicon|ENG}} Gary Neville (Manchester United)

|colspan="3"| {{flagicon|ENG}} Sol Campbell (Tottenham Hotspur)

|colspan="3"| {{flagicon|NED}} Jaap Stam (Manchester United)

|colspan="3"| {{flagicon|IRE}} Denis Irwin (Manchester United)

Midfielders

|colspan="3"| {{flagicon|ENG}} David Beckham (Manchester United)

|colspan="3"| {{flagicon|FRA|1974}} Emmanuel Petit (Arsenal)

|colspan="3"| {{flagicon|FRA|1974}} Patrick Vieira (Arsenal)

|colspan="3"| {{flagicon|FRA|1974}} David Ginola (Tottenham Hotspur)

Forwards

|colspan="6"| {{flagicon|TRI}} Dwight Yorke (Manchester United)

|colspan="6"| {{flagicon|FRA|1974}} Nicolas Anelka (Arsenal)

Notes

{{reflist}}