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| 15.07.2023 | 16:00 | Kilmarnock FC | - | Annan Athletic | 3:0 (2:0) | |
| 18:15 | Raith Rovers | - | Dunfermline Athletic | 2:4 (1:1, 1:1) i.E. | ||
| 18.07.2023 | 20:45 | Dunfermline Athletic | - | Annan Athletic | 4:0 (2:0) | |
| 20:45 | Raith Rovers | - | Albion Rovers | 2:0 (0:0) | ||
| 22.07.2023 | 16:00 | Annan Athletic | - | Albion Rovers | 1:2 (1:0) | |
| 16:00 | Dunfermline Athletic | - | Kilmarnock FC | 0:2 (0:1) | ||
| 25.07.2023 | 20:45 | Albion Rovers | - | Dunfermline Athletic | 0:3 (0:1) | |
| 26.07.2023 | 20:45 | Kilmarnock FC | - | Raith Rovers | 4:5 (1:0, 2:2) i.E. | |
| 29.07.2023 | 16:00 | Albion Rovers | - | Kilmarnock FC | 1:2 (0:2) | |
| 16:00 | Annan Athletic | - | Raith Rovers | 2:3 (2:1) |
