| League Cup | 10/10/20 | Annan Athletic | - | Stranraer FC | 4:5 pso | ||||
| League Two | 13/11/21 | Stenhousemuir FC | - | Annan Athletic | 2:0 | ||||
| League Two | 03/12/21 | Edinburgh City FC | - | Annan Athletic | 0:1 | ||||
| League Two | 02/01/22 | Stranraer FC | - | Annan Athletic | 1:1 | ||||
| League Two | 23/12/22 | Annan Athletic | - | Albion Rovers | 5:1 | ||||
| League Two | 29/04/23 | Annan Athletic | - | Bonnyrigg Rose Athletic | 0:0 | ||||
| League One | 05/08/23 | Falkirk FC | - | Annan Athletic | 3:0 | ||||
| League One | 28/11/23 | Annan Athletic | - | Hamilton Academical | 1:2 | ||||
| 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