| League Cup | 16.07.22 | Annan Athletic | - | Elgin City | 4:0 | ||||
| League Two | 20.08.22 | Annan Athletic | - | Stirling Albion FC | 1:2 | ||||
| League Two | 07.01.23 | Annan Athletic | - | Forfar Athletic | 0:2 | ||||
| Playoffs | 13.05.23 | Dumbarton FC | - | Annan Athletic | 0:0 | ||||
| League Cup | 22.07.23 | Annan Athletic | - | Albion Rovers | 1:2 | ||||
| League Cup | 23.07.24 | Dundee FC | - | Annan Athletic | 3:1 |
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