| 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 | |
Scotland