| League Two | 13.11.21 | Stenhousemuir FC | - | Annan Athletic | 2:0 | ||||
| League Two | 03.12.21 | Edinburgh City FC | - | Annan Athletic | 0:1 | ||||
| League Two | 02.01.22 | Stranraer FC | - | Annan Athletic | 1:1 |  |
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| League Two | 23.12.22 | Annan Athletic | - | Albion Rovers | 5:1 | ||||
| League Two | 29.04.23 | Annan Athletic | - | Bonnyrigg Rose Athletic | 0:0 | ||||
| League Two | 09.01.24 | Peterhead FC | - | Dumbarton FC | 3:1 | ||||
| League Cup | 16.07.24 | Queen Of The South | - | Dumbarton FC | 2:0 | |
Schottland