Primera ronda
06.08.2019 20:30 Fraserburgh FC - Ross County FC (R) 2:3 (1:1)
20:45 Hibernian FC (R) - Elgin City 3:4 (2:3)
20:45 Brora Rangers FC - Aberdeen FC (R) 6:0 (1:0)
20:45 Livingston FC (R) - Formartine United 1:3 (0:2)
20:45 Albion Rovers - Heart of Midlothian (R) 1:4 (1:2)
20:45 St. Johnstone FC (R) - Cove Rangers 1:4 (1:1)
20:45 Kelty Hearts - Kilmarnock FC (R) 4:0 (2:0)
20:45 Berwick Rangers - Rangers FC (R) 1:2 (0:2)
20:45 St. Mirren FC (R) - East Kilbride FC 1:0 (1:0)
20:45 Queen's Park FC - Celtic FC (R) 3:4 (1:2, 2:2) pn.
07.08.2019 20:45 Hamilton Academical (R) - BSC Glasgow 4:0 (1:0)
20:45 Motherwell FC (R) - Spartans FC 1:0 (1:0)
Segunda ronda
13.08.2019 20:30 Stenhousemuir FC - Edinburgh City FC 2:1 (1:0)
20:45 Heart of Midlothian (R) - Cowdenbeath FC 3:1 (0:0)
20:45 Ross County FC (R) - Raith Rovers 2:3 (0:2)
20:45 Brora Rangers FC - Cove Rangers 1:2 (0:0)
20:45 Peterhead FC - Formartine United 6:7 (0:0, 0:0) pn.
20:45 East Fife FC - Stirling Albion FC 0:2 (0:1)
20:45 Brechin City FC - Elgin City 4:5 (3:3)
20:45 Montrose FC - Forfar Athletic 2:1 (1:1)
20:45 Clyde FC - Motherwell FC (R) 4:0 (1:0)
20:45 Annan Athletic - Kelty Hearts 5:6 (1:0, 1:1) pn.
20:45 Hamilton Academical (R) - Airdrieonians 0:1 (0:1)
20:45 Dumbarton FC - St. Mirren FC (R) 0:1 (0:1)
20:45 Falkirk FC - Celtic FC (R) 6:5 (1:1, 1:1) pn.
20:45 Stranraer FC - Rangers FC (R) 0:2 (0:0)
Tercera ronda
06.09.2019 20:45 Waterford FC - Heart of Midlothian (R) 3:1 (1:0)
07.09.2019 14:00 Airdrieonians - Bohemian FC 3:2 (1:1)
16:00 Stenhousemuir FC - The New Saints 3:1 (0:0, 1:1) pn.
16:00 Wrexham AFC - Ayr United 6:5 (0:0, 1:1) pn.
16:00 Kelty Hearts - Solihull Moors 2:4 (1:0, 1:1) pn.
16:00 Formartine United - Glenavon FC 0:3 (0:1)
16:00 Inverness CT - Greenock Morton FC 3:1 (2:0)
16:00 Montrose FC - Partick Thistle 0:2 (0:1)
16:00 St. Mirren FC (R) - Stirling Albion FC 1:0 (0:0)
16:00 Dundee United - Arbroath FC 3:4 (0:0, 0:0) pn.
16:00 Clyde FC - Queen Of The South 3:2 (0:1)
16:00 Raith Rovers - Falkirk FC 2:0 (1:0)
16:00 Dunfermline Athletic - Alloa Athletic 1:2 (1:1)
18:15 Connah's Quay Nomads - Cove Rangers 1:0 (0:0)
08.09.2019 16:00 Dundee FC - Elgin City 1:2 (1:0)
18.09.2019 20:45 Ballymena United - Rangers FC (R) 0:1 (0:0)
Cuarta Ronda
11.10.2019 20:35 Stenhousemuir FC - Waterford FC 3:2 (1:1)
12.10.2019 16:00 Arbroath FC - Clyde FC 0:2 (0:1)
16:00 Airdrieonians - Elgin City 0:2 (0:0)
16:00 Raith Rovers - Glenavon FC 3:1 (2:1)
16:00 Wrexham AFC - St. Mirren FC (R) 4:1 (0:0)
16:00 Inverness CT - Alloa Athletic 3:0 (1:0)
18:15 Partick Thistle - Connah's Quay Nomads 2:0 (1:0)
29.10.2019 20:45 Solihull Moors - Rangers FC (R) 3:4 (2:1, 3:3) pn.
Cuartos de final
15.11.2019 20:45 Raith Rovers - Elgin City 3:2 (2:1)
16.11.2019 16:00 Inverness CT - Clyde FC 4:2 (0:0, 0:0) pn.
16:00 Rangers FC (R) - Wrexham AFC 2:0 (1:0)
16:00 Stenhousemuir FC - Partick Thistle 1:4 (0:1)
Semifinales
14.02.2020 20:45 Partick Thistle - Raith Rovers 1:2 (0:1)
16.02.2020 17:10 Inverness CT - Rangers FC (R) 2:1
Final
28.03.2020 Raith Rovers - Inverness CT apla.