1. Round
06/08/2019 19:30 Fraserburgh FC - Ross County FC (R) 2:3 (1:1)
19:45 Hibernian FC (R) - Elgin City 3:4 (2:3)
19:45 Brora Rangers FC - Aberdeen FC (R) 6:0 (1:0)
19:45 Livingston FC (R) - Formartine United 1:3 (0:2)
19:45 Albion Rovers - Heart of Midlothian (R) 1:4 (1:2)
19:45 St. Johnstone FC (R) - Cove Rangers 1:4 (1:1)
19:45 Kelty Hearts - Kilmarnock FC (R) 4:0 (2:0)
19:45 Berwick Rangers - Rangers FC (R) 1:2 (0:2)
19:45 St. Mirren FC (R) - East Kilbride FC 1:0 (1:0)
19:45 Queen’s Park FC - Celtic FC (R) 3:4 (1:2, 2:2) pso
07/08/2019 19:45 Hamilton Academical (R) - BSC Glasgow 4:0 (1:0)
19:45 Motherwell FC (R) - Spartans FC 1:0 (1:0)
2. Round
13/08/2019 19:30 Stenhousemuir FC - Edinburgh City FC 2:1 (1:0)
19:45 Heart of Midlothian (R) - Cowdenbeath FC 3:1 (0:0)
19:45 Ross County FC (R) - Raith Rovers 2:3 (0:2)
19:45 Brora Rangers FC - Cove Rangers 1:2 (0:0)
19:45 Peterhead FC - Formartine United 6:7 (0:0, 0:0) pso
19:45 East Fife FC - Stirling Albion FC 0:2 (0:1)
19:45 Brechin City FC - Elgin City 4:5 (3:3)
19:45 Montrose FC - Forfar Athletic 2:1 (1:1)
19:45 Clyde FC - Motherwell FC (R) 4:0 (1:0)
19:45 Annan Athletic - Kelty Hearts 5:6 (1:0, 1:1) pso
19:45 Hamilton Academical (R) - Airdrieonians FC 0:1 (0:1)
19:45 Dumbarton FC - St. Mirren FC (R) 0:1 (0:1)
19:45 Falkirk FC - Celtic FC (R) 6:5 (1:1, 1:1) pso
19:45 Stranraer FC - Rangers FC (R) 0:2 (0:0)
3. Round
06/09/2019 19:45 Waterford FC - Heart of Midlothian (R) 3:1 (1:0)
07/09/2019 13:00 Airdrieonians FC - Bohemian FC 3:2 (1:1)
15:00 Stenhousemuir FC - The New Saints 3:1 (0:0, 1:1) pso
15:00 Wrexham AFC - Ayr United 6:5 (0:0, 1:1) pso
15:00 Kelty Hearts - Solihull Moors 2:4 (1:0, 1:1) pso
15:00 Formartine United - Glenavon FC 0:3 (0:1)
15:00 Inverness CT - Greenock Morton FC 3:1 (2:0)
15:00 Montrose FC - Partick Thistle 0:2 (0:1)
15:00 St. Mirren FC (R) - Stirling Albion FC 1:0 (0:0)
15:00 Dundee United - Arbroath FC 3:4 (0:0, 0:0) pso
15:00 Clyde FC - Queen Of The South 3:2 (0:1)
15:00 Raith Rovers - Falkirk FC 2:0 (1:0)
15:00 Dunfermline Athletic - Alloa Athletic 1:2 (1:1)
17:15 Connah's Quay Nomads - Cove Rangers 1:0 (0:0)
08/09/2019 15:00 Dundee FC - Elgin City 1:2 (1:0)
18/09/2019 19:45 Ballymena United - Rangers FC (R) 0:1 (0:0)
4. Round
11/10/2019 19:35 Stenhousemuir FC - Waterford FC 3:2 (1:1)
12/10/2019 15:00 Arbroath FC - Clyde FC 0:2 (0:1)
15:00 Airdrieonians FC - Elgin City 0:2 (0:0)
15:00 Raith Rovers - Glenavon FC 3:1 (2:1)
15:00 Wrexham AFC - St. Mirren FC (R) 4:1 (0:0)
15:00 Inverness CT - Alloa Athletic 3:0 (1:0)
17:15 Partick Thistle - Connah's Quay Nomads 2:0 (1:0)
29/10/2019 19:45 Solihull Moors - Rangers FC (R) 3:4 (2:1, 3:3) pso
Quarter-finals
15/11/2019 19:45 Raith Rovers - Elgin City 3:2 (2:1)
16/11/2019 15:00 Inverness CT - Clyde FC 4:2 (0:0, 0:0) pso
15:00 Rangers FC (R) - Wrexham AFC 2:0 (1:0)
15:00 Stenhousemuir FC - Partick Thistle 1:4 (0:1)
Semi-finals
14/02/2020 19:45 Partick Thistle - Raith Rovers 1:2 (0:1)
16/02/2020 16:10 Inverness CT - Rangers FC (R) 2:1
Final
28/03/2020 Raith Rovers - Inverness CT dnp