| League Two | 05/02/22 | Annan Athletic | - | Stenhousemuir FC | 0:2 | ||||
| League Two | 26/02/22 | Kelty Hearts | - | Annan Athletic | 3:1 | ||||
| League Two | 30/07/22 | Stranraer FC | - | Annan Athletic | 1:0 | ||||
| League Two | 05/11/22 | Forfar Athletic | - | Annan Athletic | 1:4 | ||||
| League Two | 11/03/23 | Annan Athletic | - | Elgin City | 4:1 | ||||
| League One | 16/09/23 | Annan Athletic | - | Stirling Albion FC | 3:0 | ||||
| League One | 04/11/23 | Annan Athletic | - | Kelty Hearts | 2:2 | ||||
| League One | 09/12/23 | Annan Athletic | - | Cove Rangers | 1:3 | ||||
| League One | 20/04/24 | Edinburgh City | - | Annan Athletic | 1:2 | ||||
| Playoffs | 13/05/25 | East Fife FC | - | Annan Athletic | 3:2 |
Scotland