| League Cup | 23/07/19 | Raith Rovers | - | Peterhead FC | 3:1 |  |
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| League Two | 05/03/22 | Annan Athletic | - | Stranraer FC | 4:1 | ||||
| League Two | 16/04/22 | Forfar Athletic | - | Annan Athletic | 5:1 | ||||
| League Two | 06/08/22 | Annan Athletic | - | Stenhousemuir FC | 2:1 | ||||
| League Two | 28/01/23 | Annan Athletic | - | East Fife FC | 3:0 | ||||
| League Two | 22/04/23 | Stirling Albion FC | - | Annan Athletic | 3:1 |
Scotland