| League Cup | 13/10/20 | Stranraer FC | - | Albion Rovers | 14:15 pso | ||||
| League Two | 14/08/21 | Annan Athletic | - | Stirling Albion FC | 3:1 | ||||
| Playoffs | 09/05/23 | Annan Athletic | - | Dumbarton FC | 6:0 | ||||
| League One | 21/10/23 | Annan Athletic | - | Queen Of The South | 0:1 | ||||
| League One | 13/01/24 | Kelty Hearts | - | Annan Athletic | 1:1 |
Scotland