2018–19 Scottish Challenge Cup#Second round

{{Footballbox collapsible

|date=29 July 2018

|time=15:00

|team1=BSC Glasgow

|score=0–1

|report=https://spfl.co.uk/league/challenge-cup/results/996460

|team2=East Stirlingshire

|goals1=

|goals2= Tennant {{goal|50|o.g.}}

|stadium=Indodrill Stadium

|location=Alloa

|attendance=147

|referee=Chris Graham

}}

{{Footballbox collapsible

|date=1 August 2018

|time=20:00

|team1=Inverurie Loco Works

|score=2–2

|report=https://spfl.co.uk/league/challenge-cup/results/996459

|team2=Fraserburgh

|goals1=

• McCabe {{goal|37}}
• Smith {{goal|68}}

|goals2=

• Beagrie {{goal|8}}
• Campbell {{goal|84}}

|penaltyscore=5–4

|penalties1=

• Gauld {{pengoal}}
• Butcher {{pengoal}}
• Layden {{pengoal}}
• Smith {{penmiss}}
• Duff {{pengoal}}
• McCabe {{pengoal}}

|penalties2=

• {{pengoal}} Campbell
• {{pengoal}} Angus
• {{pengoal}} Christie
• {{pengoal}} Hay
• {{penmiss}} Buchan
• {{penmiss}} Rae

|stadium=Harlaw Park

|location=Inverurie

|attendance=399

|referee=Mat Northcroft

}}

The draw for the first round was made on 26 June 2018 at 1pm live on the [https://www.facebook.com/spflofficial/videos/10157412977428998/ SPFL Facebook page].

Teams in Bold advanced to the second round.

{{Footballbox collapsible

|date=14 August 2018

|time=19:45

|team1=Livingston U21s

|score=1–0
(Abandoned){{Cref2|A}}

|report=https://www.flashscore.com/match/vRwrXU2h/#match-summary

|team2=Forfar Athletic

|goals1=Watson {{goal|30}}

|goals2=

|stadium=Almondvale Stadium

|location=Livingston, Scotland

|attendance=

|referee=David Dickinson

}}

{{Footballbox collapsible

|date=14 August 2018

|time=19:45

|team1=Dundee U21s

|score=2–2

|report=https://spfl.co.uk/league/challenge-cup/results/994547

|team2=Hibernian U21s

|goals1=

• Bradbury {{goal|22}}
• Jefferies {{goal|85}}

|goals2=

• F. Murray {{goal|25}}
• Mackie {{goal|75}}

|penaltyscore=4–3

|penalties1=

• Scott {{pengoal}}
• Henvey {{pengoal}}
• Lambert {{penmiss}}
• Dow {{pengoal}}
• Bradbury {{pengoal}}

|penalties2=

• {{pengoal}} Gullan
• {{penmiss}} Stirling
• {{pengoal}} Waugh
• {{penmiss}} I. Murray
• {{pengoal}} Allan

|stadium=Dens Park

|location=Dundee, Scotland

|attendance=191

|referee=Chris Fordyce

|id=|round=}}

{{Footballbox collapsible

|date=14 August 2018

|time=19:45

|team1=Peterhead

|score=2–1

|report=https://spfl.co.uk/league/challenge-cup/results/994549

|team2=Brechin City

|goals1=

• McLean {{goal|76}}
• Leitch {{goal|86}}

|goals2=Shields {{goal|12}}

|stadium=Balmoor Stadium

|location=Peterhead, Scotland

|attendance=496

|referee=Steven Kirkland

}}

{{Footballbox collapsible

|date=14 August 2018

|time=19:45

|team1=Inverness Caledonian Thistle

|score=1–2

|report=https://spfl.co.uk/league/challenge-cup/results/994550

|team2=Dunfermline Athletic

|goals1=White {{goal|61}}

|goals2=

• Higginbotham {{goal|25|pen.}}
• Smith {{goal|87}}

|stadium=Caledonian Stadium

|location=Inverness, Scotland

|attendance=1,046

|referee=Alan Muir

}}

{{Footballbox collapsible

|date=14 August 2018

|time=19:45

|team1=Heart of Midlothian U21s

|score=1–2

|report=https://spfl.co.uk/league/challenge-cup/results/994551

|team2=Ross County

|goals1=Keena {{goal|44}}

|goals2=McKay {{goal|4||30}}

|stadium=Tynecastle Park

|location=Edinburgh, Scotland

|attendance=344

|referee=Gavin Duncan

}}

{{Footballbox collapsible

|date=14 August 2018

|time=19:45

|team1=Cowdenbeath

|score=1–3

|report=https://spfl.co.uk/league/challenge-cup/results/994557

|team2=East Fife

|goals1=Sheerin {{goal|30}}

|goals2=

• Goodfellow {{goal|68|o.g.}}
• Dowds {{goal|75}}
• Court {{goal|90}}

|stadium=Central Park

|location=Cowdenbeath, Scotland

|attendance=261

|referee=David Munro

}}

{{Footballbox collapsible

|date=14 August 2018

|time=19:45

|team1=Raith Rovers

|score=3–1

|report=https://spfl.co.uk/league/challenge-cup/results/994554

|team2=Aberdeen U21s

|goals1=

• Wedderburn {{goal|16}}
• Matthews {{goal|28}}
• Nisbet {{goal|30}}

|goals2=Anderson {{goal|72}}

|stadium=Stark's Park

|location=Kirkcaldy, Scotland

|attendance=479

|referee=Grant Irvine

}}

{{Footballbox collapsible

|date=14 August 2018

|time=19:45

|team1=Alloa Athletic

|score=3–1

|report=https://spfl.co.uk/league/challenge-cup/results/994555

|team2=Stirling Albion

|goals1=

• Cawley {{goal|40||45}}
• Flannigan {{goal|46}}

|goals2=Hamilton {{goal|55}}

|stadium=Recreation Park

|location=Alloa, Scotland

|attendance=332

|referee=David Lowe

}}

{{Footballbox collapsible

|date=14 August 2018

|time=20:00

|team1=Inverurie Loco Works

|score=0–1

|report=https://spfl.co.uk/league/challenge-cup/results/994548

|team2=Formartine United

|goals1=

|goals2=Gethins {{goal|61}}

|stadium=Harlaw Park

|location=Inverurie, Scotland

|attendance=399

|referee=Mike Roncone

}}

{{Footballbox collapsible

|date=15 August 2018

|time=19:45

|team1=Cove Rangers

|score=2–2

|report=https://spfl.co.uk/league/challenge-cup/results/994556

|team2=Montrose

|goals1=McManus {{goal|44||49}}

|goals2=

• I. Campbell {{goal|34|pen.}}
• Callaghan {{goal|69}}

|penaltyscore=3–4

|penalties1=

• Meggison {{pengoal}}
• McManus {{pengoal}}
• McKenzie {{penmiss}}
• Masson {{pengoal}}
• Brown {{penmiss}}

|penalties2=

• {{pengoal}} I. Campbell
• {{penmiss}} Fotheringham
• {{pengoal}} Steeves
• {{pengoal}} R. Campbell
• {{pengoal}} Johnston

|stadium=Balmoral Stadium

|location=Cove Bay, Scotland

|attendance=420

|referee=Graham Beaton

}}

{{Footballbox collapsible

|date=15 August 2018

|time=19:45

|team1=Elgin City

|score=1–1

|report=https://spfl.co.uk/league/challenge-cup/results/994552

|team2=Arbroath

|goals1=O'Brien {{goal|57}}

|goals2=McHardy {{goal|83}}

|penaltyscore=6–7

|penalties1=

• McGovern {{pengoal}}
• McHardy {{pengoal}}
• Sutherland {{pengoal}}
• Cameron {{penmiss}}
• McLeish {{pengoal}}
• Lowdon {{pengoal}}
• Byrne {{pengoal}}
• Cooper {{penmiss}}

|penalties2=

• {{pengoal}} Wallace
• {{pengoal}} Hamilton
• {{penmiss}} Linn
• {{pengoal}} McCord
• {{pengoal}} Swankie
• {{pengoal}} Thomson
• {{pengoal}} Denholm
• {{pengoal}} Gold

|stadium=Borough Briggs

|location=Elgin, Scotland

|attendance=401

|referee=Scott Lambie

}}

{{Footballbox collapsible

|date=15 August 2018

|time=19:45

|team1=Dundee United

|score=3–2

|report=https://spfl.co.uk/league/challenge-cup/results/994553

|team2=St Johnstone U21s

|goals1=

• Chalmers {{goal|64}}
• McMullan {{goal|78||90+2}}

|goals2=Hendry {{goal|21||58}}

|stadium=Tannadice Park

|location=Dundee, Scotland

|attendance=700

|referee=Colin Steven

}}

;Notes

{{Cnote2 Begin|liststyle=disc}}

{{Cnote2|A|A-The Livingston U21s-Forfar Athletic match was abandoned with Livingston U21s leading 1–0 after 71 minutes due poor lighting caused by a power outage. The match was replayed on 21 August 2018.}}

{{Cnote2 End}}

{{Footballbox collapsible

|date=21 August 2018

|time=19:45

|team1=Livingston U21s

|score=0–0

|report=https://spfl.co.uk/league/challenge-cup/results/994546

|team2=Forfar Athletic

|goals1=

|goals2=

|penaltyscore=5–4

|penalties1=

• Jacobs {{pengoal}}
• McMillan {{pengoal}}
• Clark {{pengoal}}
• Hamilton {{pengoal}}
• Watson {{penmiss}}
• Thomson {{pengoal}}

|penalties2=

• {{pengoal}} Munro
• {{pengoal}} Meechan
• {{pengoal}} Whyte
• {{penmiss}} Baird
• {{pengoal}} Bain
• {{penmiss}} Malone

|stadium=Almondvale Stadium

|location=Livingston, Scotland

|attendance=460

|referee=David Dickinson

}}

Teams in Bold advanced to the second round.

{{Footballbox collapsible

|date=14 August 2018

|time=19:00

|team1=Kilmarnock U21s

|score=1–2

|report=https://spfl.co.uk/league/challenge-cup/results/994562

|team2=St Mirren U21s

|goals1=

• Thomas {{goal|48}}

|goals2=

• Jamieson {{goal|10}}
• MacPherson {{goal|55}}

|stadium=Rugby Park

|location=Kilmarnock, Scotland

|attendance=208

|referee=Stephen Brown

}}

{{Footballbox collapsible

|date=14 August 2018

|time=19:30

|team1=Stenhousemuir

|score=0–3

|report=https://spfl.co.uk/league/challenge-cup/results/994560

|team2=Queen of the South

|goals1=

|goals2=

• Dobbie {{goal|59||66}}
• Dykes {{goal|62}}

|stadium=Ochilview Park

|location=Stenhousemuir, Scotland

|attendance=387

|referee=Kevin Graham

}}

{{Footballbox collapsible

|date=14 August 2018

|time=19:30

|team1=Rangers U21s

|score=1–2

|report=https://spfl.co.uk/league/challenge-cup/results/994569

|team2=Falkirk

|goals1=

• Rudden {{goal|90}}

|goals2=

• Lewis {{goal|4}}
• Harrison {{goal|21}}

|stadium=Forthbank Stadium

|location=Stirling, Scotland

|attendance=636

|referee=Euan Anderson

}}

{{Footballbox collapsible

|date=14 August 2018

|time=19:45

|team1=Queen's Park

|score=0–0

|report=https://spfl.co.uk/league/challenge-cup/results/994559

|team2=Ayr United

|goals1=

|goals2=

|penaltyscore=4–2

|penalties1=

• McKernon {{penmiss}}
• Gibson {{pengoal}}
• Mortimer {{pengoal}}
• Roberts {{pengoal}}
• Osadolor {{pengoal}}

|penalties2=

• {{pengoal}} Rose
• {{penmiss}} Murdoch
• {{pengoal}} Shankland
• {{penmiss}} Forrest

|stadium=Hampden Park

|location=Glasgow, Scotland

|attendance=834

|referee=Greg Aitken

}}

{{Footballbox collapsible

|date=14 August 2018

|time=19:45

|team1=Hamilton Academical U21s

|score=4–1

|report=https://spfl.co.uk/league/challenge-cup/results/994561

|team2=Clyde

|goals1=

• Enigbokan-Bloomfield {{goal|8||90}}
• Cunningham {{goal|62}}
• Hughes {{goal|73}}

|goals2=McStay {{goal|9}}

|stadium=New Douglas Park

|location=Hamilton, Scotland

|attendance=297

|referee=Chris Graham

}}

{{Footballbox collapsible

|date=14 August 2018

|time=19:45

|team1=East Stirlingshire

|score=0–3

|report=https://spfl.co.uk/league/challenge-cup/results/994563

|team2=Motherwell U21s

|goals1=

|goals2=

• Turnbull {{goal|16}}
• Watson {{goal|20}}
• Hastie {{goal|22}}

|stadium=Falkirk Stadium

|location=Falkirk, Scotland

|attendance=150

|referee=Duncan Smith

}}

{{Footballbox collapsible

|date=14 August 2018

|time=19:45

|team1=Annan Athletic

|score=4–0

|report=https://spfl.co.uk/league/challenge-cup/results/994564

|team2=Celtic U21s

|goals1=

• Wallace {{goal|9}}
• Fergusson {{goal|55||67||81}}

|goals2=

|stadium=Galabank

|location=Annan, Scotland

|attendance=266

|referee=Lloyd Wilson

}}

{{Footballbox collapsible

|date=14 August 2018

|time=19:45

|team1=Edinburgh City

|score=3–1

|report=https://spfl.co.uk/league/challenge-cup/results/994565

|team2=Albion Rovers

|goals1=

• Shepherd {{goal|70}}
• Henderson {{goal|77||83|pen.}}

|goals2=Cunningham {{goal|15}}

|stadium=Ainslie Park

|location=Edinburgh, Scotland

|attendance=182

|referee=Steven Reid

}}

{{Footballbox collapsible

|date=14 August 2018

|time=19:45

|team1=Stranraer

|score=0–5

|report=https://spfl.co.uk/league/challenge-cup/results/994566

|team2=Partick Thistle

|goals1=

|goals2=

• O'Ware {{goal|10}}
• Fitzpatrick {{goal|34||90+2}}
• Mbuyi-Mutombo {{goal|36}}
• Melbourne {{goal|89}}

|stadium=Stair Park

|location=Stranraer, Scotland

|attendance=480

|referee=Alan Newlands

}}

{{Footballbox collapsible

|date=14 August 2018

|time=19:45

|team1=Dumbarton

|score=2–1

|report=https://spfl.co.uk/league/challenge-cup/results/994567

|team2=Greenock Morton

|goals1=

• Paton {{goal|12}}
• Russell {{goal|26}}

|goals2=Oliver {{goal|39}}

|stadium=Dumbarton Football Stadium

|location=Dumbarton, Scotland

|attendance=680

|referee=Gavin Ross

}}

{{Footballbox collapsible

|date=14 August 2018

|time=19:45

|team1=Berwick Rangers

|score=0–3

|report=https://spfl.co.uk/league/challenge-cup/results/994568

|team2=Airdrieonians

|goals1=

|goals2=

• Conroy {{goal|2}}
• Carrick {{goal|19}}
• McIntosh {{goal|22|pen.}}

|stadium=Shielfield Park

|location=Berwick-upon-Tweed, England

|attendance=317

|referee=John McKendrick

}}

{{Footballbox collapsible

|date=15 August 2018

|time=19:45

|team1=East Kilbride

|score=1–1

|report=https://spfl.co.uk/league/challenge-cup/results/994558

|team2=Spartans

|goals1=McNeil {{goal|61}}

|goals2=Cennarazo {{goal|3}}

|penaltyscore=5–4

|penalties1=

• Winter {{pengoal}}
• Malcolm {{pengoal}}
• Longworth {{pengoal}}
• Reid {{pengoal}}
• Coll {{pengoal}}

|penalties2=

• {{pengoal}} Corbett
• {{pengoal}} Stevenson
• {{penmiss}} Smith
• {{pengoal}} Herd
• {{pengoal}} Maxwell

|stadium=K-Park Training Academy

|location=East Kilbride, Scotland

|attendance=207

|referee=Duncan Williams

}}

Teams from Wales (The New Saints and Connah's Quay Nomads), Northern Ireland (Crusaders and Coleraine), England (Sutton United and Boreham Wood) and the Republic of Ireland (Bohemians and Sligo Rovers) entered in the second round.{{cite web |url=https://spfl.co.uk/news/article/national-league-sides-join-irn-bru-cup/ |title=National League sides join IRN-BRU Cup |publisher=SPFL |work=spfl.co.uk |date=8 June 2018 |access-date=8 June 2018 |archive-date=12 June 2018 |archive-url=https://web.archive.org/web/20180612143325/https://spfl.co.uk/news/article/national-league-sides-join-irn-bru-cup/ |url-status=dead }} Originally, Bray Wanderers were to be the second side to represent the League of Ireland however, they were subsequently thrown out by the FAI on 16 July 2018 for failing to pay their players and replaced by Limerick.{{cite web |url=http://leagueofireland.ie/index.php/2018/07/16/bray-wanderers-thrown-out-of-irn-bru-cup-and-banned-from-signing-players/ |title=Bray Wanderers thrown out of IRN BRU Cup and banned from signing players |publisher=League of Ireland |work=leagueofireland.ie |date=16 July 2018 |access-date=29 July 2018}} A similar statement was released by the FAI hours later about Limerick who were also in financial difficulties.{{cite web |url=http://leagueofireland.ie/index.php/2018/07/16/deja-vu-fai-release-statement-on-limerick-fc/ |title=Deja Vu? FAI release statement on Limerick FC |publisher=League of Ireland |work=leagueofireland.ie |date=16 July 2018 |access-date=29 July 2018}} St Patrick's Athletic were then invited to compete as the next ranked team in line but declined. Sligo Rovers accepted the position in their place so they would represent the League of Ireland instead.{{cite web |url=https://www.irishmirror.ie/sport/soccer/soccer-news/sligo-rovers-play-seasons-scottish-13016365 |title=Sligo Rovers to play in this season's Scottish Challenge Cup |publisher=Irish Mirror |work=irishmirror.ie |date=1 August 2018 |access-date=1 August 2018}}

The draw for the second round was made on 16 August 2018 at 1pm live on the [https://www.facebook.com/spflofficial/videos/10157563037478998/ SPFL Facebook page].

Teams in Bold advanced to the third round.

Teams in Italics were not known at the time of the draw.

{{Footballbox collapsible

|date=6 September 2018

|time=19:00

|team1=Dundee U21s

|score=1–2

|report=https://spfl.co.uk/league/challenge-cup/results/1018968

|team2=Motherwell U21s

|goals1=Armstrong {{goal|43|o.g.}}

|goals2=

• MacDonald {{goal|25}}
• Watson {{goal|86}}

|stadium=Dens Park

|location=Dundee, Scotland

|attendance=208

|referee=Mike Roncone

}}

{{Footballbox collapsible

|date=8 September 2018

|time=13:00

|team1=Boreham Wood

|score=0–0

|report=https://spfl.co.uk/league/challenge-cup/results/1018958

|team2=Dunfermline Athletic

|goals1=

|goals2=

|penaltyscore=5–6

|penalties1=

• Murtagh {{pengoal}}
• Umerah {{pengoal}}
• Fyfield {{pengoal}}
• Ilesanmi {{pengoal}}
• Hackett-Fairchild {{pengoal}}
• C. Smith {{penmiss}}

|penalties2=

• {{pengoal}} M. Martin
• {{pengoal}} Craigen
• {{pengoal}} Hippolyte
• {{pengoal}} El Bakhtaoui
• {{pengoal}} Connolly
• {{pengoal}} Muirhead

|stadium=Meadow Park

|location=Borehamwood, England

|attendance=1,001

|referee=Evan Boyce

}}

{{Footballbox collapsible

|date=8 September 2018

|time=14:30

|team1=Queen of the South

|score=4–3

|report=https://spfl.co.uk/league/challenge-cup/results/1018961

|team2=Crusaders

|goals1=

• Dobbie {{goal|22||31}}
• Dykes {{goal|25}}
• Harkins {{goal|29}}

|goals2=

• Patterson {{goal|47||51|pen.}}
• Heatley {{goal|85}}

|stadium=Palmerston Park

|location=Dumfries, Scotland

|attendance=1,204

|referee=Damian McGrath

}}

{{Footballbox collapsible

|date=8 September 2018

|time=15:00

|team1=Falkirk

|score=0–1

|report=https://spfl.co.uk/league/challenge-cup/results/1018957

|team2=Connah's Quay Nomads

|goals1=

|goals2=Wilde {{goal|46}}

|stadium=Falkirk Stadium

|location=Falkirk, Scotland

|attendance=1,637

|referee=Daniel Middleton

}}

{{Footballbox collapsible

|date=8 September 2018

|time=15:00

|team1=Airdrieonians

|score=0–1

|report=https://spfl.co.uk/league/challenge-cup/results/1018959

|team2=Sutton United

|goals1=

|goals2=Wright {{goal|21}}

|stadium=Excelsior Stadium

|location=Airdrie, Scotland

|attendance=831

|referee=Mark Petch

}}

{{Footballbox collapsible

|date=8 September 2018

|time=15:00

|team1=Peterhead

|score=0–1

|report=https://spfl.co.uk/league/challenge-cup/results/1018963

|team2=Bohemians

|goals1=

|goals2=Devaney {{goal|63}}

|stadium=Balmoor Stadium

|location=Peterhead, Scotland

|attendance=713

|referee=Sam Purkiss

}}

{{Footballbox collapsible

|date=8 September 2018

|time=15:00

|team1=East Fife

|score=2–1

|report=https://spfl.co.uk/league/challenge-cup/results/1018964

|team2=Partick Thistle

|goals1=

• Agnew {{goal|51}}
• Currie {{goal|74}}

|goals2=Mbuyi-Mutombo {{goal|22}}

|stadium=Bayview Stadium

|location=Methil, Scotland

|attendance=932

|referee=Alan Muir

}}

{{Footballbox collapsible

|date=8 September 2018

|time=15:00

|team1=Arbroath

|score=3–0

|report=https://spfl.co.uk/league/challenge-cup/results/1018965

|team2=Annan Athletic

|goals1=

• Linn {{goal|8}}
• Denholm {{goal|71}}
• McKenna {{goal|83}}

|goals2=

|stadium=Gayfield Park

|location=Arbroath, Scotland

|attendance=524

|referee=Colin Steven

}}

{{Footballbox collapsible

|date=8 September 2018

|time=15:00

|team1=Dumbarton

|score=0–1

|report=https://spfl.co.uk/league/challenge-cup/results/1018966

|team2=Montrose

|goals1=

|goals2=Johnston {{goal|19}}

|stadium=Dumbarton Football Stadium

|location=Dumbarton, Scotland

|attendance=456

|referee=David Munro

}}

{{Footballbox collapsible

|date=8 September 2018

|time=15:00

|team1=Dundee United

|score=1–1

|report=https://spfl.co.uk/league/challenge-cup/results/1018967

|team2=Alloa Athletic

|goals1=Smith {{goal|15}}

|goals2=Trouten {{goal|78|pen.}}

|penaltyscore=4–5

|penalties1=

• Fyvie {{pengoal}}
• Thomas {{penmiss}}
• Glass {{pengoal}}
• McMullan {{pengoal}}
• Smith {{pengoal}}

|penalties2=

• {{pengoal}} Taggart
• {{pengoal}} Flannigan
• {{pengoal}} Zanatta
• {{pengoal}} Trouten
• {{pengoal}} Graham

|stadium=Tannadice Park

|location=Dundee, Scotland

|attendance=1,040

|referee=Greg Aitken

}}

{{Footballbox collapsible

|date=8 September 2018

|time=15:00

|team1=East Kilbride

|score=2–3

|report=https://spfl.co.uk/league/challenge-cup/results/1018969

|team2=Edinburgh City

|goals1=

• McNeil {{goal|72}}
• Malcolm {{goal|73}}

|goals2=

• Henderson {{goal|36}}
• Smith {{goal|84||86}}

|stadium=K-Park Training Academy

|location=East Kilbride, Scotland

|attendance=287

|referee=Steven Kirkland

}}

{{Footballbox collapsible

|date=8 September 2018

|time=15:00

|team1=St Mirren U21s

|score=3–2

|report=https://spfl.co.uk/league/challenge-cup/results/1018970

|team2=Hamilton Academical U21s

|goals1=

• Jamieson {{goal|10}}
• MacPherson {{goal|39|pen.}}
• Potter {{goal|70}}

|goals2=

• A. Smith {{goal|27}}
• L. Smith {{goal|87}}

|stadium=St Mirren Park

|location=Paisley, Scotland

|attendance=316

|referee=Graham Beaton

}}

{{Footballbox collapsible

|date=8 September 2018

|time=15:00

|team1=Ross County

|score=5–0

|report=https://spfl.co.uk/league/challenge-cup/results/1018971

|team2=Raith Rovers

|goals1=

• Graham {{goal|18||29||40||42}}
• Lindsay {{goal|37}}

|goals2=

|stadium=Victoria Park

|location=Dingwall, Scotland

|attendance=1,232{{cite web |url=http://www.raithrovers.net/fixtures-past |title=Season 2018-2019 |work=Raith Rovers FC |access-date=10 September 2018}}

|referee=John Beaton

}}

{{Footballbox collapsible

|date=8 September 2018

|time=19:35

|team1=The New Saints

|score=2–2

|report=https://spfl.co.uk/league/challenge-cup/results/1018956

|team2=Queen's Park

|goals1=

• Hart {{goal|30|o.g.}}
• Nembhard {{goal|90+5}}

|goals2=

• Osadolor {{goal|89}}
• Hawke {{goal|90+1}}

|penaltyscore=2–4

|penalties1=

• Mullan {{penmiss}}
• Brobbel {{penmiss}}
• Ebbe {{pengoal}}
• Marriott {{pengoal}}

|penalties2=

• {{pengoal}} McLean
• {{penmiss}} Gibson
• {{pengoal}} Foy
• {{pengoal}} Roberts
• {{pengoal}} Peters

|stadium=Park Hall

|location=Oswestry, England

|attendance=278

|referee=Bernard Connolly

}}

{{Footballbox collapsible

|date=8 September 2018

|time=19:45

|team1=Coleraine

|score=1–1

|report=https://spfl.co.uk/league/challenge-cup/results/1018960

|team2=Formartine United

|goals1=Carson {{goal|31}}

|goals2=MacPhee {{goal|20}}

|penaltyscore=2–1

|penalties1=

• Parkhill {{penmiss}}
• Carson {{penmiss}}
• McConaghie {{pengoal}}
• Bradley {{pengoal}}

|penalties2=

• {{penmiss}} S. Anderson
• {{penmiss}} Fraser
• {{penmiss}} MacPhee
• {{pengoal}} Greig
• {{penmiss}} Gethins

|stadium=The Showgrounds

|location=Coleraine, Northern Ireland

|attendance=973

|referee=David Morgan

}}

{{Footballbox collapsible

|date=8 September 2018

|time=19:45

|team1=Sligo Rovers

|score=4–1

|report=https://spfl.co.uk/league/challenge-cup/results/1018962

|team2=Livingston U21s

|goals1=

• Drennan {{goal|15||52||86}}
• Cawley {{goal|60}}

|goals2=Knox {{goal|3}}

|stadium=The Showgrounds

|location=Sligo, Ireland

|attendance=408{{cite tweet |user=sligorovers |number=1038519338578464768 |date=8 September 2018 |title=Sligo Rovers v Livingston Colts attendance}}

|referee=Lee Tavinder

}}

The draw for the third round was made on 11 September 2018 at 1pm live on the [https://www.facebook.com/spflofficial/videos/551608921939116/ SPFL Facebook page].

Teams in Bold advanced to the quarter-finals.

{{Footballbox collapsible

|date=12 October 2018

|time=19:35

|team1=Arbroath

|score=1–4

|report=https://spfl.co.uk/league/challenge-cup/results/1023433

|team2=Edinburgh City

|goals1=McKenna {{goal|11}}

|goals2=

• B. Henderson {{goal|25|pen.|68|pen.}}
• Shepherd {{goal|56}}
• L. Henderson {{goal|78}}

|stadium=Gayfield Park

|location=Arbroath, Scotland

|attendance=506

|referee=Alan Muir

}}

{{Footballbox collapsible

|date=13 October 2018

|time=15:00

|team1=East Fife

|score=2–0

|report=https://spfl.co.uk/league/challenge-cup/results/1023432

|team2=Queen of the South

|goals1=

• Smith {{goal|34}}
• Dowds {{goal|78}}

|goals2=

|stadium=Bayview Stadium

|location=Methil, Scotland

|attendance=579

|referee=Barry Cook

}}

{{Footballbox collapsible

|date=13 October 2018

|time=15:00

|team1=Bohemians

|score=0–0

|report=https://spfl.co.uk/league/challenge-cup/results/1023434

|team2=Sutton United

|goals1=

|goals2=

|penaltyscore=4–3

|penalties1=

• Lunney {{pengoal}}
• Pender {{pengoal}}
• Brennan {{penmiss}}
• Stokes {{penmiss}}
• Supple {{pengoal}}
• Cornwall {{pengoal}}

|penalties2=

• {{pengoal}} Lafayette
• {{pengoal}} Davis
• {{pengoal}} Drinan
• {{penmiss}} Cadogan
• {{penmiss}} Eastmond
• {{penmiss}} Thomas

|stadium=Dalymount Park

|location=Dublin, Ireland

|attendance=1,130

|referee=Mike Roncone

}}

{{Footballbox collapsible

|date=13 October 2018

|time=15:00

|team1=Dunfermline Athletic

|score=2–2

|report=https://spfl.co.uk/league/challenge-cup/results/1023435

|team2=Alloa Athletic

|goals1=L. Longridge {{goal|28||47|pen.}}

|goals2=Trouten {{goal|8||70}}

|penaltyscore=4–5

|penalties1=

• Craigen {{pengoal}}
• L. Longridge {{pengoal}}
• Hippolyte {{pengoal}}
• Beadling {{pengoal}}
• Connolly {{penmiss}}

|penalties2=

• {{pengoal}} Taggart
• {{pengoal}} Flannigan
• {{pengoal}} Zanatta
• {{pengoal}} Trouten
• {{pengoal}} Graham

|stadium=East End Park

|location=Dunfermline, Scotland

|attendance=1,469

|referee=Nick Walsh

}}

{{Footballbox collapsible

|date=13 October 2018

|time=15:00

|team1=Ross County

|score=3–1

|report=https://spfl.co.uk/league/challenge-cup/results/1023436

|team2=Montrose

|goals1=

• Stewart {{goal|20}}
• Keillor-Dunn {{goal|41||51}}

|goals2=Johnston {{goal|44}}

|stadium=Victoria Park

|location=Dingwall, Scotland

|attendance=1,122

|referee=Craig Napier

}}

{{Footballbox collapsible

|date=13 October 2018

|time=15:00

|team1=St Mirren U21s

|score=2–4

|report=https://spfl.co.uk/league/challenge-cup/results/1023437

|team2=Queen's Park

|goals1=

• Jamieson {{goal|2}}
• Breadner {{goal|63}}

|goals2=

• Hawke {{goal|61}}
• McLean {{goal|66||82|pen.}}
• East {{goal|80}}

|stadium=St Mirren Park

|location=Paisley, Scotland

|attendance=507

|referee=Grant Irvine

}}

{{Footballbox collapsible

|date=13 October 2018

|time=15:00

|team1=Motherwell U21s

|score=2–0

|report=https://spfl.co.uk/league/challenge-cup/results/1023438

|team2=Sligo Rovers

|goals1=

• McClean {{goal|12|o.g.}}
• Mbulu {{goal|71}}

|goals2=

|stadium=Fir Park

|location=Motherwell, Scotland

|attendance=950

|referee=Richard Hulme

}}

{{Footballbox collapsible

|date=13 October 2018

|time=19:30

|team1=Connah's Quay Nomads

|score=2–0

|report=https://spfl.co.uk/league/challenge-cup/results/1023439

|team2=Coleraine

|goals1=

• Horan {{goal|61}}
• Owens {{goal|90}}

|goals2=

|stadium=Deeside Stadium

|location=Connah's Quay, Wales

|attendance=624

|referee=Colin Steven

}}

The draw for the quarter-finals was made on 16 October 2018 at 1pm at The Hub in Edinburgh live on the [https://www.facebook.com/spflofficial/videos/877470965791912 SPFL Facebook page].{{cite web |url=https://spfl.co.uk/news/irn-bru-cup-draw-live-on-tuesday |title=IRN-BRU CUP DRAW LIVE ON TUESDAY |publisher=Scottish Professional Football League |work=spfl.co.uk |date=15 October 2018 |access-date=15 October 2018}}

Teams in Bold advanced to the semi-finals.

{{Footballbox collapsible

|date=16 November 2018

|time=19:45

|team1=Queen's Park

|score=1–2

|report=https://spfl.co.uk/league/challenge-cup/results/1031859

|team2=Connah's Quay Nomads

|goals1=Hawke {{goal|64}}

|goals2=

• Horan {{goal|81}}
• Wilde {{goal|84}}

|stadium=Hampden Park

|location=Glasgow, Scotland

|attendance=559

|referee=David Rock

}}

{{Footballbox collapsible

|date=17 November 2018

|time=15:00

|team1=Edinburgh City

|score=2–2

|report=

|team2=Alloa Athletic

|goals1=

• B. Henderson {{goal|45}}
• Shepherd {{goal|57}}

|goals2=

• Zanatta {{goal|2}}
• Trouten {{goal|12}}

|penaltyscore=4–3

|penalties1=

• L. Henderson {{pengoal}}
• Laird {{pengoal}}
• Smith {{pengoal}}
• Thomson {{pengoal}}

|penalties2=

• {{penmiss}} Taggart
• {{pengoal}} Flannigan
• {{pengoal}} Zanatta
• {{pengoal}} Trouten
• {{penmiss}} Graham

|stadium=Ainslie Park

|location=Edinburgh, Scotland

|attendance=478

|referee=Don Robertson

}}

{{Footballbox collapsible

|date=17 November 2018

|time=15:00

|team1=Motherwell U21s

|score=1–2

|report=https://spfl.co.uk/league/challenge-cup/results/1031856

|team2=Ross County

|goals1=Livingstone {{goal|53}}

|goals2=Stewart {{goal|51||56}}

|stadium=Fir Park

|location=Motherwell, Scotland

|attendance=1,209

|referee=David Munro

}}

{{Footballbox collapsible

|date=2 February 2019

|time=15:00

|team1=Bohemians

|score=w/o{{Cref2|B}}

|report=https://www.bbc.co.uk/sport/football/47036369

|team2=East Fife

|goals1=

|goals2=

|stadium=Dalymount Park

|location=Dublin, Ireland

|attendance=

|referee=

}}

;Notes

{{Cnote2 Begin|liststyle=disc}}

{{Cnote2|B|B-The Bohemians-East Fife match was originally due to take place on 17 November 2018 but was rearranged as the Irish football season had finished. It was rearranged to be played on 2 February 2019 but was called off due to a frozen pitch at 14:53, seven minutes before kick-off.{{cite web |url=https://www.bbc.co.uk/sport/football/47036369 |title=Challenge Cup: Bohemians v East Fife called off seven minutes before kick-off |publisher=BBC Sport |work=bbc.co.uk/sport |date=2 February 2019 |access-date=4 February 2019}} Following discussions with the SPFL in an attempt to rearrange the fixture again, Bohemians withdrew from the competition and East Fife advanced to the semi-finals.{{cite web |url=https://www.bbc.co.uk/sport/football/47119171 |title=Bohemians withdraw from Challenge Cupfollowing late call-off of East Fife tie |publisher=BBC Sport |work=bbc.co.uk/sport |date=4 February 2019 |access-date=4 February 2019}}}}

{{Cnote2 End}}

The draw for the semi-finals was made on 21 November 2018 at 1pm at Hampden Park live on the [https://www.facebook.com/spflofficial/videos/260084971369308/ SPFL Facebook page].{{cite web |url=https://spfl.co.uk/news/irn-bru-cup-draw-today |title=IRN-BRU CUP SEMI-FINAL DRAW |publisher=Scottish Professional Football League |work=spfl.co.uk |date=21 November 2018 |access-date=21 November 2018}}

{{Footballbox collapsible

|date=15 February 2019

|time=19:45

|team1=Ross County

|score=2–1

|report=https://www.bbc.co.uk/sport/football/47201776

|team2=East Fife

|goals1=Armstrong {{goal|18}}
McManus {{goal|37}}

|goals2=*Dowds {{goal|39}}

|stadium=Victoria Park

|location=Dingwall, Scotland

|attendance=1,283

|referee=Alan Newlands

}}

{{Footballbox collapsible

|date=16 February 2019

|time=19:25

|team1=Connah's Quay Nomads

|score=1–1

|aet=yes

|penaltyscore=5–4

|penalties1=

• Morris {{pengoal}}
• Harrison {{pengoal}}
• Disney {{pengoal}}
• Bakare {{pengoal}}
• Wilde {{penmiss}}
• Horan {{pengoal}}

|penalties2=

• {{pengoal}} L.Henderson
• {{pengoal}} Laird
• {{pengoal}} Donaldson
• {{penmiss}} Thomson
• {{pengoal}} B.Henderson
• {{penmiss}} Diver

|report=https://www.bbc.co.uk/sport/football/47254752

|team2=Edinburgh City

|goals1=Wilde {{goal|18}}

|goals2=Walker {{goal|2}}

|stadium=Deeside Stadium

|location=Connah's Quay, Wales

|attendance=1,068

|referee=James Oldham

}}

{{main|2019 Scottish Challenge Cup Final}}

{{Footballbox collapsible

|date=23 March 2019

|time=16:30

|team1=Ross County

|score=3–1

|report=https://www.bbc.co.uk/sport/football/47622909

|team2=Connah's Quay Nomads

|goals1=Mullin {{goal|75}}, {{goal|78}}
Lindsay {{goal|86}}

|goals2=Bakare {{goal|22}}

|stadium=Caledonian Stadium

|location=Inverness, Scotland

|attendance=3,057

|referee=Alan Muir

}}

The Golden Ball Award is a 'Player of the Round' award given to the player who is adjudged to have had the best performance of that round out of all the players in teams left competing in that round of the competition. The winner is voted for by supporters from a chosen short-list of players, which is posted on the Irn-Bru Football Twitter page.

The domestic broadcasting rights for the competition are held jointly by BBC Alba, S4C (for matches involving Welsh teams) and subscription channel Premier Sports. Prior to the re-format in the 2016–17 season, BBC Alba had exclusive rights.{{cite web|title=Challenge Cup expansion announced|url=http://spfl.co.uk/news/article/spfl-announces-challenge-cup-expansion/|publisher=Scottish Professional Football League|date=8 June 2016|access-date=8 June 2018|archive-date=7 November 2017|archive-url=https://web.archive.org/web/20171107112345/https://spfl.co.uk/news/article/spfl-announces-challenge-cup-expansion/|url-status=dead}}

One of the semi-final matches was also confirmed as being broadcast live on BT Sport despite no apparent previous announcement of rights.

The following matches were broadcast live on UK television:

{{reflist}}

• [https://web.archive.org/web/20180612162300/https://spfl.co.uk/challenge-cup/ Scottish Challenge Cup at the Scottish Professional Football League]

{{Scottish Challenge Cup seasons}}

{{2018–19 in Scottish football}}

{{2018–19 in Northern Ireland association football}}

{{DEFAULTSORT:2018-19 Scottish Challenge Cup}}

Category:Scottish Challenge Cup seasons

Challenge Cup

Challenge Cup

Category:2018–19 in Northern Ireland association football

Category:2018–19 in Welsh football