1. Runde
20.09.2019 20:05 Kelty Hearts - Auchinleck Talbot 0:3 (0:2)
21.09.2019 16:00 Broxburn Athletic - East Stirlingshire FC 3:2 (2:1)
16:00 Buckie Thistle - Civil Service Strollers 4:1 (3:0)
16:00 Caledonian Braves - Rothes FC 3:4 (0:2)
16:00 Cumbernauld Colts - Penicuik Athletic 1:5 (0:3)
16:00 Dalbeattie Star - Gala Fairydean Rovers 1:3 (0:2)
16:00 Edinburgh University AFC - Lochee United FC 1:3 (0:0)
16:00 Forres Mechanics FC - Banks O’ Dee FC 1:4 (0:0)
16:00 Fort William FC - Vale of Leithen FC 5:0 (1:0)
16:00 Fraserburgh FC - Bonnyrigg Rose Athletic 0:1 (0:0)
16:00 Gretna FC 2008 - Hill of Beath Hawthorn 1:0 (0:0)
16:00 Inverurie Loco Works - Wick Academy FC 3:2 (0:2)
16:00 Linlithgow Rose - Huntly FC 1:0 (0:0)
16:00 Keith FC - University of Stirling FC 2:3 (0:1)
16:00 Nairn County FC - Clachnacuddin FC 0:0 (0:0)
16:00 The Spartans FC - Deveronvale FC 1:1 (1:1)
16:00 Strathspey Thistle FC - Lossiemouth FC 2:1 (1:0)
16:00 Turriff United - Formartine United 1:5 (0:3)
28.09.2019 16:00 Clachnacuddin FC - Nairn County FC 2:1 (1:0)
30.09.2019 21:00 Deveronvale FC - The Spartans FC 1:2 (1:1)
2. Runde
18.10.2019 20:05 Bonnyrigg Rose Athletic - Buckie Thistle 2:0 (0:0)
20:30 Edinburgh City FC - Banks O’ Dee FC 3:1 (2:1)
19.10.2019 15:30 Auchinleck Talbot - Cove Rangers 1:0 (0:0)
16:00 Stirling Albion FC - Strathspey Thistle FC 2:0 (2:0)
16:00 Lochee United FC - BSC Glasgow 1:1 (1:0)
16:00 Annan Athletic - Brechin City FC 2:2 (2:0)
16:00 Formartine United - Gala Fairydean Rovers 2:2 (0:1)
16:00 Elgin City - Berwick Rangers 3:1 (1:1)
16:00 Rothes FC - Inverurie Loco Works 1:3 (0:2)
16:00 Cowdenbeath FC - Broxburn Athletic 1:1 (0:0)
16:00 East Kilbride FC - Gretna FC 2008 3:1 (2:1)
16:00 Albion Rovers - Fort William FC 1:1 (1:0)
16:00 The Spartans FC - Queen's Park FC 0:2 (0:2)
16:00 Clachnacuddin FC - Brora Rangers FC 0:7 (0:4)
20.10.2019 16:00 University of Stirling FC - Linlithgow Rose 0:2 (0:0)
26.10.2019 15:30 Penicuik Athletic - Stenhousemuir FC 3:0 (0:0)
16:00 Brechin City FC - Annan Athletic 0:2 (0:0)
16:00 Gala Fairydean Rovers - Formartine United 1:2 (0:0)
16:00 Broxburn Athletic - Cowdenbeath FC 3:0 (1:0)
16:00 Fort William FC - Albion Rovers 0:5 (0:4)
27.10.2019 16:30 BSC Glasgow - Lochee United FC 2:1 (1:0)
3. Runde
22.11.2019 20:05 Linlithgow Rose - Falkirk FC 1:4 (1:2)
23.11.2019 14:45 Auchinleck Talbot - Arbroath FC 1:1 (1:0)
16:00 Albion Rovers - Airdrieonians FC 1:4 (0:1)
16:00 Bonnyrigg Rose Athletic - Montrose FC 2:1 (2:1)
16:00 Dumbarton FC - Forfar Athletic 3:1 (1:1)
16:00 East Fife FC - BSC Glasgow 3:4 (2:1)
16:00 Edinburgh City FC - Annan Athletic 4:3 (3:0)
16:00 Elgin City - Alloa Athletic 1:3 (1:0)
16:00 Formartine United - East Kilbride FC 0:4 (0:1)
16:00 Greenock Morton FC - Brora Rangers FC 1:1 (1:1)
16:00 Inverurie Loco Works - Broxburn Athletic 0:1 (0:0)
16:00 Partick Thistle - Penicuik Athletic 1:0 (1:0)
16:00 Queen Of The South - Queen's Park FC 1:2 (0:2)
16:00 Raith Rovers - Peterhead FC 1:0 (1:0)
16:00 Stirling Albion FC - Clyde FC 0:2 (0:1)
16:00 Stranraer FC - Dunfermline Athletic 1:0 (0:0)
27.11.2019 20:45 Arbroath FC - Auchinleck Talbot 3:0 (1:0)
03.12.2019 20:45 Brora Rangers FC - Greenock Morton FC 1:3 (0:1)
4. Runde
17.01.2020 20:45 Rangers FC - Stranraer FC 2:0 (1:0)
18.01.2020 16:00 St. Mirren FC - Broxburn Athletic 3:0 (0:0)
16:00 Kilmarnock FC - Queen's Park FC 6:0 (3:0)
16:00 Heart of Midlothian - Airdrieonians FC 5:0 (1:0)
16:00 Alloa Athletic - Inverness CT 2:3 (1:1)
16:00 Livingston FC - Raith Rovers 3:1 (0:1)
16:00 Arbroath FC - Falkirk FC 0:0 (0:0)
16:00 Ayr United - Ross County FC 1:0 (1:0)
16:00 Aberdeen FC - Dumbarton FC 1:0 (0:0)
16:00 Bonnyrigg Rose Athletic - Clyde FC 0:1 (0:0)
16:00 St. Johnstone FC - Greenock Morton FC 3:0 (1:0)
16:00 Hamilton Academical - Edinburgh City FC 5:0 (3:0)
16:00 East Kilbride FC - BSC Glasgow 1:3 (0:3)
18:30 Partick Thistle - Celtic FC 1:2 (0:1)
20:20 Dundee FC - Motherwell FC 0:3 (0:2)
19.01.2020 16:00 Dundee United - Hibernian FC 2:2 (1:1)
28.01.2020 20:45 Falkirk FC - Arbroath FC 2:0 (0:0)
20:45 Hibernian FC - Dundee United 4:2 (1:1)
Achtelfinale
08.02.2020 13:30 Hamilton Academical - Rangers FC 1:4 (1:1)
16:00 Aberdeen FC - Kilmarnock FC 0:0 (0:0)
16:00 Ayr United - St. Johnstone FC 1:2 (1:2)
16:00 Inverness CT - Livingston FC 1:0 (0:0)
16:00 St. Mirren FC - Motherwell FC 1:1 (0:1)
20:20 Falkirk FC - Heart of Midlothian 0:1 (0:0)
09.02.2020 13:00 BSC Glasgow - Hibernian FC 1:4 (1:2)
15:00 Clyde FC - Celtic FC 0:3 (0:2)
18.02.2020 20:45 Motherwell FC - St. Mirren FC 2:3 (1:4, 4:4, 4:4) i.E.
19.02.2020 20:45 Kilmarnock FC - Aberdeen FC 3:4 (1:0, 1:1) n.V.
Viertelfinale
28.02.2020 20:45 Hibernian FC - Inverness CT 5:2 (1:0)
29.02.2020 18:30 Heart of Midlothian - Rangers FC 1:0 (0:0)
20:20 St. Mirren FC - Aberdeen FC 0:2 (0:1)
01.03.2020 16:00 St. Johnstone FC - Celtic FC 0:1 (0:0)
Halbfinale
31.10.2020 18:00 Heart of Midlothian - Hibernian FC 2:1 (0:0, 1:1) n.V.
01.11.2020 15:30 Celtic FC - Aberdeen FC 2:0 (2:0)
Finale
20.12.2020 15:15 Celtic FC - Heart of Midlothian 4:3 (2:0, 2:2, 3:3) i.E.