| 2024-05-04 15:00:0004/05/2024 | Stirling | 1 - 1 | Annan | Scottish League One | N/A |
| 2024-04-27 15:00:0027/04/2024 | Annan | 3 - 3 | Falkirk | Scottish League One | N/A |
| 2024-04-20 15:00:0020/04/2024 | Edinburgh City | 1 - 2 | Annan | Scottish League One | N/A |
| 2024-04-13 15:00:0013/04/2024 | Annan | 4 - 2 | Cove | Scottish League One | N/A |
| 2024-04-06 15:00:0006/04/2024 | Annan | 1 - 3 | Hamilton | Scottish League One | N/A |
| 2024-03-30 15:00:0030/03/2024 | Alloa | 1 - 1 | Annan | Scottish League One | N/A |
| 2024-03-23 15:00:0023/03/2024 | Annan | 3 - 2 | Kelty | Scottish League One | N/A |
| 2024-03-16 15:00:0016/03/2024 | Montrose | 1 - 1 | Annan | Scottish League One | N/A |
| 2024-03-09 15:00:0009/03/2024 | Annan | 2 - 1 | QOTS | Scottish League One | N/A |
| 2024-03-02 15:00:0002/03/2024 | Falkirk | 1 - 1 | Annan | Scottish League One | N/A |
| 2024-02-24 15:00:0024/02/2024 | Cove | 2 - 1 | Annan | Scottish League One | N/A |
| 2024-02-17 15:00:0017/02/2024 | Annan | 2 - 1 | Stirling | Scottish League One | N/A |
| 2024-02-13 19:45:0013/02/2024 | Alloa | 2 - 1 | Annan | Scottish League One | N/A |
| 2024-02-10 15:00:0010/02/2024 | Hamilton | 2 - 3 | Annan | Scottish League One | N/A |
| 2024-02-03 15:00:0003/02/2024 | Annan | 2 - 3 | Alloa | Scottish League One | N/A |
| 2024-01-27 15:00:0027/01/2024 | Annan | 3 - 0 | Edinburgh City | Scottish League One | N/A |
| 2024-01-13 15:00:0013/01/2024 | Kelty | 1 - 1 | Annan | Scottish League One | N/A |
| 2024-01-06 15:00:0006/01/2024 | Annan | 2 - 2 | Montrose | Scottish League One | N/A |
| 2023-12-30 15:00:0030/12/2023 | QOTS | 2 - 1 | Annan | Scottish League One | N/A |
| 2023-12-23 15:00:0023/12/2023 | Annan | 0 - 3 | Falkirk | Scottish League One | N/A |
| 2023-12-16 15:00:0016/12/2023 | Stirling | 1 - 1 | Annan | Scottish League One | N/A |
| 2023-12-09 15:00:0009/12/2023 | Annan | 1 - 3 | Cove | Scottish League One | N/A |
| 2023-11-28 19:45:0028/11/2023 | Annan | 1 - 2 | Hamilton | Scottish League One | N/A |
| 2023-11-25 15:00:0025/11/2023 | Annan | 4 - 5 | Dumbarton | Scottish Cup | N/A |
| 2023-11-11 15:00:0011/11/2023 | Montrose | 1 - 1 | Annan | Scottish League One | N/A |
| 2023-11-04 15:00:0004/11/2023 | Annan | 2 - 2 | Kelty | Scottish League One | N/A |
| 2023-10-28 15:00:0028/10/2023 | Edinburgh City | 3 - 2 | Annan | Scottish League One | N/A |
| 2023-10-21 15:00:0021/10/2023 | Annan | 0 - 1 | QOTS | Scottish League One | N/A |
| 2023-10-07 15:00:0007/10/2023 | Cove | 3 - 2 | Annan | Scottish League One | N/A |
| 2023-09-29 19:45:0029/09/2023 | Hamilton | 5 - 0 | Annan | Scottish League One | N/A |
| 2023-09-23 15:00:0023/09/2023 | Annan | 1 - 1 | Alloa | Scottish League One | N/A |
| 2023-09-16 15:00:0016/09/2023 | Annan | 3 - 0 | Stirling | Scottish League One | N/A |
| 2023-09-09 15:00:0009/09/2023 | Annan | 0 - 2 | Peterhead | Scottish Challenge Cup | N/A |
| 2023-09-02 15:00:0002/09/2023 | Kelty | 1 - 1 | Annan | Scottish League One | N/A |
| 2023-08-26 15:00:0026/08/2023 | Annan | 3 - 2 | Edinburgh City | Scottish League One | N/A |
| 2023-08-19 15:00:0019/08/2023 | QOTS | 3 - 1 | Annan | Scottish League One | N/A |
| 2023-08-15 19:45:0015/08/2023 | Annan | 3 - 1 | Stranraer | Scottish Challenge Cup | N/A |
| 2023-08-12 15:00:0012/08/2023 | Annan | 1 - 3 | Montrose | Scottish League One | N/A |
| 2023-08-05 15:00:0005/08/2023 | Falkirk | 3 - 0 | Annan | Scottish League One | N/A |
| 2023-07-29 15:00:0029/07/2023 | Annan | 2 - 3 | Raith | Scottish League Cup | N/A |
| 2023-07-22 15:00:0022/07/2023 | Annan | 1 - 2 | Albion | Scottish League Cup | N/A |
| 2023-07-18 19:45:0018/07/2023 | Dunfermline | 4 - 0 | Annan | Scottish League Cup | N/A |
| 2023-07-15 15:00:0015/07/2023 | Kilmarnock | 3 - 0 | Annan | Scottish League Cup | N/A |
| 2023-07-07 19:45:0007/07/2023 | Annan | 1 - 2 | Carlisle | Club Friendly | N/A |
| 2023-07-04 19:45:4804/07/2023 | Annan | 0 - 1 | Morton | Club Friendly | N/A |
