Phong độ của Annan Athletic |
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| 05.08.2023 | Falkirk | 3-0 | Annan Athletic |  | ||
| 29.07.2023 | Annan Athletic | 2-3 | Raith Rovers | | ||
| 22.07.2023 | Annan Athletic | 1-2 | Albion Rovers | | ||
| 19.07.2023 | Dunfermline Athletic | 4-0 | Annan Athletic | | ||
| 15.07.2023 | Kilmarnock | 3-0 | Annan Athletic | | ||
| 08.07.2023 | Annan Athletic | 1-2 | Carlisle United | | ||
| 05.07.2023 | Annan Athletic | 0-1 | Greenock Morton | | ||
| 20.05.2023 | Clyde | 1-2 | Annan Athletic | | ||
| 17.05.2023 | Annan Athletic | 3-1 | Clyde | | ||
| 13.05.2023 | Dumbarton | 0-0 | Annan Athletic | | ||
Phong độ của Montrose |
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| 05.08.2023 | Montrose | 0-2 | Kelty Hearts | | ||
| 29.07.2023 | Arbroath | 3-0 | Montrose | | ||
| 22.07.2023 | Cowdenbeath | 1-1 | Montrose | | ||
| 19.07.2023 | Montrose | 1-2 | Forfar Athletic | | ||
| 15.07.2023 | Montrose | 1-0 | Saint Mirren | | ||
| 08.07.2023 | Montrose | 5-2 | Civil Service Strollers FC | | ||
| 01.07.2023 | Arbroath | 1-3 | Montrose | | ||
| 01.07.2023 | Montrose | 1-3 | Forfar Athletic | | ||
| 28.06.2023 | Montrose | 1-3 | Raith Rovers | | ||
| 06.05.2023 | Clyde | 2-1 | Montrose | | ||