| League Cup | 19.07.22 | Annan Athletic | - | Ayr United | 5:4 pn. | ||||
| League Two | 29.10.22 | Annan Athletic | - | Dumbarton FC | 0:1 | ||||
| League Two | 21.01.23 | Annan Athletic | - | Bonnyrigg Rose Athletic | 4:0 | ||||
| League Two | 15.04.23 | Annan Athletic | - | Albion Rovers | 4:0 | ||||
| League Cup | 18.07.23 | Dunfermline Athletic | - | Annan Athletic | 4:0 | ||||
| League One | 07.10.23 | Cove Rangers | - | Annan Athletic | 3:2 | ||||
| League One | 17.02.24 | Annan Athletic | - | Stirling Albion FC | 2:1 | ||||
| League One | 30.03.24 | Alloa Athletic | - | Annan Athletic | 1:1 | ||||
| League One | 25.01.25 | Queen Of The South | - | Dumbarton FC | 3:1 |
Guadalupe