| League Cup | 19/07/22 | Annan Athletic | - | Ayr United | 5:4 pso | ||||
| 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 Two | 04/11/23 | Stranraer FC | - | Elgin City | 3:1 |
Scotland