| League Two | 03.12.22 | East Fife FC | - | Annan Athletic | 1:3 | ||||
| League Two | 25.03.23 | Annan Athletic | - | Stranraer FC | 0:0 | ||||
| League Two | 06.05.23 | Stenhousemuir FC | - | Annan Athletic | 2:1 | ||||
| League One | 03.02.24 | Annan Athletic | - | Alloa Athletic | 2:3 |  |
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| League Two | 15.03.25 | Elgin City | - | Clyde FC | 2:0 | ||||
| League Two | 12.04.25 | Clyde FC | - | Forfar Athletic | 1:1 |
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