| League Two | 16.10.21 | Forfar Athletic | - | Annan Athletic | 2:0 | ||||
| League Two | 05.11.22 | Albion Rovers | - | Stirling Albion FC | 1:1 |  |
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| League Two | 04.02.23 | Elgin City | - | Albion Rovers | 1:1 | |
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| League Two | 04.05.24 | Stranraer FC | - | Stenhousemuir FC | 2:0 | ||||
| League Cup | 23.07.24 | Dundee FC | - | Annan Athletic | 3:1 |
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