Home History
| Scotland League One | 2023/09/16 14:00 | Annan Athletic v Stirling | W | 3-0 |
| Scotland League Challenge Cup | 2023/09/09 14:00 | Annan Athletic v Peterhead | L | 0-2 |
| Scotland League One | 2023/09/02 14:00 | Kelty Hearts v Annan Athletic | D | 1-1 |
| Scotland League One | 2023/08/26 14:00 | Annan Athletic v FC Edinburgh | W | 3-2 |
| Scotland League One | 2023/08/19 14:00 | Queen of South v Annan Athletic | L | 3-1 |
| Scotland League Challenge Cup | 2023/08/15 18:45 | Annan Athletic v Stranraer | W | 3-1 |
| Scotland League One | 2023/08/12 14:00 | Annan Athletic v Montrose | L | 1-3 |
| Scotland League One | 2023/08/05 14:00 | Falkirk v Annan Athletic | L | 3-0 |
Away History
| Scotland League One | 2023/09/16 14:00 | Hamilton v Alloa | L | 2-1 |
| Scotland League One | 2023/09/02 14:00 | Alloa v Cove Rangers | W | 1-0 |
| Scotland League One | 2023/08/26 16:30 | Alloa v Falkirk | L | 1-4 |
| Scotland League One | 2023/08/19 14:00 | Kelty Hearts v Alloa | L | 2-1 |
| Scotland League One | 2023/08/12 14:00 | Alloa v Stirling | L | 0-1 |
| Scotland League One | 2023/08/05 14:00 | Queen of South v Alloa | W | 3-4 |
| Scotland League Cup | 2023/07/29 14:00 | Ayr v Alloa | L | 6-0 |
| Scotland League Cup | 2023/07/25 18:45 | Stenhousemuir v Alloa | W | 1-3 |