Tour préliminaire
29.07.2018 16:00 BSC Glasgow - East Stirlingshire FC 0:1
01.08.2018 21:00 Inverurie Loco Works - Fraserburgh FC 5:4 (1:1, 2:2) tab
1er tour
14.08.2018 20:00 Kilmarnock FC (R) - St. Mirren FC (R) 1:2 (0:1)
20:30 Heart of Midlothian (R) - Ross County FC 1:2 (1:2)
20:30 Stenhousemuir FC - Queen Of The South 0:3 (0:0)
20:30 Rangers FC (R) - Falkirk FC 1:2 (0:2)
20:45 Dundee FC (R) - Hibernian FC (R) 2:1 (1:1, 2:2) tab
20:45 Peterhead FC - Brechin City FC 2:1 (0:1)
20:45 Inverness CT - Dunfermline Athletic 1:2 (0:1)
20:45 Raith Rovers - Aberdeen FC (R) 3:1 (3:0)
20:45 Alloa Athletic - Stirling Albion FC 3:1 (2:0)
20:45 Cowdenbeath FC - East Fife FC 1:3 (1:0)
20:45 Queen's Park FC - Ayr United 4:2 (0:0, 0:0) tab
20:45 Hamilton Academical (R) - Clyde FC 4:1 (1:1)
20:45 East Stirlingshire FC - Motherwell FC (R) 0:3 (0:3)
20:45 Annan Athletic - Celtic FC (R) 4:0 (1:0)
20:45 Edinburgh City FC - Albion Rovers 3:1 (0:1)
20:45 Stranraer FC - Partick Thistle 0:5 (0:3)
20:45 Dumbarton FC - Greenock Morton FC 2:1 (2:1)
20:45 Berwick Rangers - Airdrieonians FC 0:3 (0:3)
21:00 Inverurie Loco Works - Formartine United 0:1 (0:0)
15.08.2018 20:45 Elgin City - Arbroath FC 6:7 (0:0, 1:1) tab
20:45 Dundee United - St. Johnstone FC (R) 3:2 (0:1)
20:45 Cove Rangers - Montrose FC 3:4 (1:1, 2:2) tab
20:45 East Kilbride FC - The Spartans FC 5:4 (0:1, 1:1) tab
21.08.2018 20:45 Livingston FC (R) - Forfar Athletic 5:4 (0:0, 0:0) tab
2e tour
06.09.2018 20:00 Dundee FC (R) - Motherwell FC (R) 1:2 (1:1)
08.09.2018 14:00 Boreham Wood - Dunfermline Athletic 5:6 (0:0, 0:0) tab
15:30 Queen Of The South - Crusaders FC 4:3 (4:0)
16:00 Falkirk FC - Connah's Quay Nomads 0:1 (0:0)
16:00 Airdrieonians FC - Sutton United 0:1 (0:1)
16:00 Peterhead FC - Bohemian FC 0:1 (0:0)
16:00 East Fife FC - Partick Thistle 2:1 (0:1)
16:00 Arbroath FC - Annan Athletic 3:0 (1:0)
16:00 Dumbarton FC - Montrose FC 0:1 (0:1)
16:00 Dundee United - Alloa Athletic 4:5 (1:0, 1:1) tab
16:00 East Kilbride FC - Edinburgh City FC 2:3 (0:1)
16:00 St. Mirren FC (R) - Hamilton Academical (R) 3:2 (2:1)
16:00 Ross County FC - Raith Rovers 5:0 (5:0)
20:35 The New Saints - Queen's Park FC 2:4 (1:0, 2:2) tab
20:45 Coleraine FC - Formartine United 2:1 (1:1, 1:1) tab
20:45 Sligo Rovers - Livingston FC (R) 4:1 (1:1)
tour des 16
12.10.2018 20:35 Arbroath FC - Edinburgh City FC 1:4 (1:1)
13.10.2018 16:00 East Fife FC - Queen Of The South 2:0 (1:0)
16:00 Bohemian FC - Sutton United 4:3 (0:0, 0:0) tab
16:00 Dunfermline Athletic - Alloa Athletic 4:5 (1:1, 2:2) tab
16:00 Ross County FC - Montrose FC 3:1 (2:1)
16:00 St. Mirren FC (R) - Queen's Park FC 2:4 (1:0)
16:00 Motherwell FC (R) - Sligo Rovers 2:0 (1:0)
20:30 Connah's Quay Nomads - Coleraine FC 2:0 (0:0)
Quarts de finale
16.11.2018 20:45 Queen's Park FC - Connah's Quay Nomads 1:2 (0:0)
17.11.2018 16:00 Motherwell FC (R) - Ross County FC 1:2 (0:0)
16:00 Edinburgh City FC - Alloa Athletic 4:3 (1:2, 2:2) tab
02.02.2019 Bohemian FC - East Fife FC pas disputer
Demi-finales
15.02.2019 20:45 Ross County FC - East Fife FC 2:1 (2:1)
16.02.2019 20:25 Connah's Quay Nomads - Edinburgh City FC 5:4 (1:1, 1:1, 1:1) tab
Finale
23.03.2019 17:30 Connah's Quay Nomads - Ross County FC 1:3 (1:0)