| League Two | 21.08.21 | Albion Rovers | - | Annan Athletic | 0:1 |  |
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| League Two | 30.10.21 | Annan Athletic | - | Cowdenbeath FC | 1:0 | ||||
| FA Cup | 27.11.21 | Gala Fairydean Rovers | - | Annan Athletic | 0:1 | ||||
| League Two | 03.09.22 | Annan Athletic | - | Forfar Athletic | 2:1 | ||||
| League One | 12.08.23 | Annan Athletic | - | Montrose FC | 1:3 | ||||
| League One | 02.09.23 | Kelty Hearts | - | Annan Athletic | 1:1 | |
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| League Two | 05.10.24 | Clyde FC | - | The Spartans FC | 1:1 | ||||
| League Two | 07.12.24 | Clyde FC | - | Peterhead FC | 3:2 | ||||
| League Two | 17.01.25 | Clyde FC | - | Edinburgh City | 0:2 |
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