| League Cup | 06/10/20 | Annan Athletic | - | Hamilton Academical | 3:1 | ||||
| League Two | 26/12/21 | Annan Athletic | - | Kelty Hearts | 5:1 | ||||
| League Cup | 25/07/23 | Kelty Hearts | - | Stranraer FC | 2:0 | ||||
| Playoffs | 18/05/24 | Stranraer FC | - | East Kilbride FC | 3:1 aet | ||||
| League One | 28/12/24 | Queen Of The South | - | Annan Athletic | 1:1 | ||||
| League One | 18/01/25 | Annan Athletic | - | Inverness CT | 0:3 |
Scotland