| League Cup | 19/07/22 | Annan Athletic | - | Ayr United | 5:4 pso | ||||
| League Two | 29/10/22 | Annan Athletic | - | Dumbarton FC | 0:1 | ||||
| League Two | 15/04/23 | Annan Athletic | - | Albion Rovers | 4:0 | ||||
| League Cup | 18/07/23 | Dunfermline Athletic | - | Annan Athletic | 4:0 |  |
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| League One | 07/10/23 | Cove Rangers | - | Annan Athletic | 3:2 | ||||
| League One | 17/02/24 | Annan Athletic | - | Stirling Albion FC | 2:1 | ||||
| League One | 30/03/24 | Alloa Athletic | - | Annan Athletic | 1:1 |
Scotland