| League One | 05/08/23 | Falkirk FC | - | Annan Athletic | 3:0 | ||||
| League One | 27/01/24 | Annan Athletic | - | Edinburgh City | 3:0 | ||||
| League One | 13/04/24 | Annan Athletic | - | Cove Rangers | 4:2 | ||||
| League One | 24/08/24 | Annan Athletic | - | Alloa Athletic | 0:1 | ||||
| League One | 22/02/25 | Annan Athletic | - | Alloa Athletic | 3:4 |
Scotland