| League Two | 05/02/22 | Annan Athletic | - | Stenhousemuir FC | 0:2 | ||||
| League Two | 26/02/22 | Kelty Hearts | - | Annan Athletic | 3:1 | ||||
| League Two | 30/07/22 | Stranraer FC | - | Annan Athletic | 1:0 | ||||
| League Two | 05/11/22 | Forfar Athletic | - | Annan Athletic | 1:4 | ||||
| League Two | 11/03/23 | Annan Athletic | - | Elgin City | 4:1 |  |
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| League Two | 13/04/24 | Dumbarton FC | - | Clyde FC | 1:0 | |
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| Playoffs | 07/05/24 | Dumbarton FC | - | Stirling Albion FC | 2:1 |  |
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| League One | 10/08/24 | Dumbarton FC | - | Alloa Athletic | 3:3 |
Scotland