| 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 |
Scotland