| League Cup | 15.07.17 | Clyde FC | - | Annan Athletic | 2:1 | ||||
| League Cup | 17.07.18 | Annan Athletic | - | Berwick Rangers | 4:0 | ||||
| League Two | 12.11.22 | Stirling Albion FC | - | Annan Athletic | 0:2 | ||||
| League Two | 11.02.23 | Dumbarton FC | - | Annan Athletic | 2:1 | ||||
| League One | 23.09.23 | Annan Athletic | - | Alloa Athletic | 1:1 |  |
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| League One | 27.04.24 | Annan Athletic | - | Falkirk FC | 3:3 | |
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| League One | 31.08.24 | Stenhousemuir FC | - | Annan Athletic | 5:1 | |
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