| League Cup | 10.11.20 | Albion Rovers | - | Annan Athletic | 1:5 |  |
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| League Two | 02.04.22 | Stenhousemuir FC | - | Annan Athletic | 0:1 | ||||
| League Two | 30.07.22 | Stenhousemuir FC | - | Albion Rovers | 1:0 | ||||
| League Two | 27.08.22 | Albion Rovers | - | Annan Athletic | 2:2 | ||||
| League Two | 27.04.24 | Forfar Athletic | - | Stranraer FC | 2:0 | ||||
| Playoffs | 11.05.24 | East Kilbride FC | - | Stranraer FC | 2:2 | ||||
| League One | 14.12.24 | Dumbarton FC | - | Annan Athletic | 1:5 | ||||
| League One | 15.02.25 | Cove Rangers | - | Annan Athletic | 3:1 |
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