| Championship | 29/12/20 | Raith Rovers | - | Queen Of The South | 0:2 |  |
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| League Two | 28/08/21 | Cowdenbeath FC | - | Annan Athletic | 1:3 | ||||
| League Two | 19/02/22 | Annan Athletic | - | Edinburgh City FC | 2:1 | ||||
| League Two | 30/04/22 | Annan Athletic | - | Kelty Hearts | 1:2 | ||||
| League Two | 13/08/22 | Dumbarton FC | - | Annan Athletic | 4:0 |  |
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| League Two | 17/09/22 | Annan Athletic | - | East Fife FC | 2:2 | |
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| League Two | 04/03/23 | Annan Athletic | - | Stenhousemuir FC | 2:3 | |
England