1. Round
01/08/2023 19:30 Elgin City - St. Johnstone FC (R) 2:0 (1:0)
19:30 Brechin City FC - Heart of Midlothian (R) 5:3 (2:0, 2:2) pso
19:30 St. Mirren FC (R) - Albion Rovers 2:4 (0:2, 2:2) pso
19:45 Tranent FC - Motherwell FC (R) 3:1 (0:0, 0:0) pso
19:45 The Spartans FC - Rangers FC (R) 0:3 (0:1)
19:45 Kilmarnock FC (R) - Bonnyrigg Rose Athletic 3:1 (2:0)
02/08/2023 19:30 Hibernian FC (R) - Formartine United 4:2 (1:1, 1:1) pso
19:45 Brora Rangers FC - Aberdeen FC (R) 2:4 (1:0, 1:1) pso
19:45 University of Stirling FC - Livingston FC (R) 4:0 (1:0)
19:45 Celtic FC (R) - East Kilbride FC 1:3 (1:1)
20:00 Dundee FC (R) - Buckie Thistle 4:0 (3:0)
2. Round
15/08/2023 19:30 Brechin City FC - Hibernian FC (R) 0:4 (0:2)
19:45 Annan Athletic - Stranraer FC 3:1 (1:1)
19:45 Elgin City - Forfar Athletic 4:3 (0:0, 0:0) pso
19:45 Aberdeen FC (R) - Peterhead FC 3:5 (1:0)
19:45 Dundee FC (R) - East Fife FC 3:5 (0:0, 0:0) pso
19:45 Stirling Albion FC - East Kilbride FC 0:3 (0:1)
19:45 Albion Rovers - Tranent FC 2:0 (0:0)
19:45 Stenhousemuir FC - Rangers FC (R) 1:2 (0:0)
16/08/2023 19:45 Kilmarnock FC (R) - Dumbarton FC 8:9 (0:1, 1:1) pso
19:45 Clyde FC - University of Stirling FC 1:3 (0:1)
3. Round
05/09/2023 19:45 Ayr United - Falkirk FC 0:1 (0:1)
08/09/2023 18:00 Hibernian FC (R) - The New Saints 0:3 (0:2)
09/09/2023 13:00 East Fife FC - Albion Rovers 2:1 (0:1)
14:00 Raith Rovers - Cliftonville FC 3:0 (0:0)
15:00 Edinburgh City - East Kilbride FC 1:4 (0:1)
15:00 Annan Athletic - Peterhead FC 0:2 (0:1)
15:00 Cove Rangers - Montrose FC 0:2 (0:0)
15:00 Dumbarton FC - Kelty Hearts 1:3 (1:2)
15:00 University of Stirling FC - Airdrieonians FC 2:3 (1:2)
15:00 Greenock Morton FC - Elgin City 2:1 (1:1)
15:00 Dundee United - Dunfermline Athletic 3:0 (3:0)
15:00 Arbroath FC - Inverness CT 4:2 (2:1)
15:00 Partick Thistle - Queen Of The South 2:3 (1:2)
15:45 Coleraine FC - Hamilton Academical 1:3 (1:1)
17:15 Bala Town - Queen's Park FC 0:3 (0:2)
26/09/2023 19:45 Rangers FC (R) - Alloa Athletic 4:1 (1:1)
Round of 16
14/10/2023 15:00 Raith Rovers - Montrose FC 3:1 (1:0)
15:00 East Kilbride FC - Hamilton Academical 2:5 (1:4)
15:00 Falkirk FC - Queen's Park FC 1:0 (1:0)
15:00 Queen Of The South - Arbroath FC 1:2 (1:0)
15:00 Greenock Morton FC - Kelty Hearts 4:1 (1:1)
17:15 The New Saints - East Fife FC 5:4 (1:1, 2:2) pso
17:30 Peterhead FC - Dundee United 0:2 (0:1)
07/11/2023 19:45 Rangers FC (R) - Airdrieonians FC 2:4 (1:2)
Quarter-finals
17/11/2023 19:40 Falkirk FC - Dundee United 4:2 (1:2)
19:45 Hamilton Academical - Raith Rovers 1:4 (0:1)
18/11/2023 14:30 The New Saints - Arbroath FC 4:1 (2:1)
15:00 Greenock Morton FC - Airdrieonians FC 5:6 (0:0, 0:0) pso
Semi-finals
02/02/2024 19:40 Raith Rovers - Airdrieonians FC 0:1 (0:1)
03/02/2024 19:40 Falkirk FC - The New Saints 0:1 (0:1)
Final
24/03/2024 16:15 The New Saints - Airdrieonians FC 1:2 (1:1)
Challenge Cup
Challenge Cup

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