| 2024-04-20 15:00:0020/04/2024 15:00 | Edinburgh City | 15:00:0015:00 | Annan | Scottish League One | N/A |
| 2024-04-13 15:00:0013/04/2024 15:00 | Annan | 15:00:0015:00 | Cove | Scottish League One | N/A |
| 2024-04-06 15:00:0006/04/2024 15:00 | Annan | 15:00:0015:00 | Hamilton | Scottish League One | N/A |
| 2024-03-30 15:00:0030/03/2024 15:00 | Alloa | 15:00:0015:00 | Annan | Scottish League One | N/A |
| 2024-03-23 15:00:0023/03/2024 15:00 | Annan | 15:00:0015:00 | Kelty | Scottish League One | N/A |
| 2024-03-16 15:00:0016/03/2024 15:00 | Montrose | 15:00:0015:00 | Annan | Scottish League One | N/A |
| 2024-03-09 15:00:0009/03/2024 15:00 | Annan | 15:00:0015:00 | QOTS | Scottish League One | N/A |
| 2024-03-02 15:00:0002/03/2024 15:00 | Falkirk | 15:00:0015:00 | Annan | Scottish League One | N/A |
| 2024-02-24 15:00:0024/02/2024 15:00 | Cove | 15:00:0015:00 | Annan | Scottish League One | N/A |
| 2024-02-17 15:00:0017/02/2024 15:00 | Annan | 15:00:0015:00 | Stirling | Scottish League One | N/A |
| 2024-02-13 19:45:0013/02/2024 19:45 | Alloa | 19:45:0019:45 | Annan | Scottish League One | N/A |
| 2024-02-10 15:00:0010/02/2024 15:00 | Hamilton | 15:00:0015:00 | Annan | Scottish League One | N/A |
| 2024-02-03 15:00:0003/02/2024 15:00 | Annan | 15:00:0015:00 | Alloa | Scottish League One | N/A |
| 2024-01-27 15:00:0027/01/2024 15:00 | Annan | 15:00:0015:00 | Edinburgh City | Scottish League One | N/A |
| 2024-01-13 15:00:0013/01/2024 15:00 | Kelty | 15:00:0015:00 | Annan | Scottish League One | N/A |
| 2024-01-06 15:00:0006/01/2024 15:00 | Annan | 2 - 2 | Montrose | Scottish League One | N/A |
| 2023-12-30 15:00:0030/12/2023 15:00 | QOTS | 2 - 1 | Annan | Scottish League One | N/A |
| 2023-12-23 15:00:0023/12/2023 15:00 | Annan | 0 - 3 | Falkirk | Scottish League One | N/A |
| 2023-12-16 15:00:0016/12/2023 15:00 | Stirling | 1 - 1 | Annan | Scottish League One | N/A |
| 2023-12-09 15:00:0009/12/2023 15:00 | Annan | 1 - 3 | Cove | Scottish League One | N/A |
| 2023-11-28 19:45:0028/11/2023 19:45 | Annan | 1 - 2 | Hamilton | Scottish League One | N/A |
| 2023-11-25 15:00:0025/11/2023 15:00 | Annan | 4 - 5 | Dumbarton | Scottish Cup | N/A |
| 2023-11-11 15:00:0011/11/2023 15:00 | Montrose | 1 - 1 | Annan | Scottish League One | N/A |
| 2023-11-04 15:00:0004/11/2023 15:00 | Annan | 2 - 2 | Kelty | Scottish League One | N/A |
| 2023-10-28 15:00:0028/10/2023 15:00 | Edinburgh City | 3 - 2 | Annan | Scottish League One | N/A |
| 2023-10-21 15:00:0021/10/2023 15:00 | Annan | 0 - 1 | QOTS | Scottish League One | N/A |
| 2023-10-07 15:00:0007/10/2023 15:00 | Cove | 3 - 2 | Annan | Scottish League One | N/A |
| 2023-09-29 19:45:0029/09/2023 19:45 | Hamilton | 5 - 0 | Annan | Scottish League One | N/A |
| 2023-09-23 15:00:0023/09/2023 15:00 | Annan | 1 - 1 | Alloa | Scottish League One | N/A |
| 2023-09-16 15:00:0016/09/2023 15:00 | Annan | 3 - 0 | Stirling | Scottish League One | N/A |
| 2023-09-09 15:00:0009/09/2023 15:00 | Annan | 0 - 2 | Peterhead | Scottish Challenge Cup | N/A |
| 2023-09-02 15:00:0002/09/2023 15:00 | Kelty | 1 - 1 | Annan | Scottish League One | N/A |
| 2023-08-26 15:00:0026/08/2023 15:00 | Annan | 3 - 2 | Edinburgh City | Scottish League One | N/A |
| 2023-08-19 15:00:0019/08/2023 15:00 | QOTS | 3 - 1 | Annan | Scottish League One | N/A |
| 2023-08-15 19:45:0015/08/2023 19:45 | Annan | 3 - 1 | Stranraer | Scottish Challenge Cup | N/A |
| 2023-08-12 15:00:0012/08/2023 15:00 | Annan | 1 - 3 | Montrose | Scottish League One | N/A |
| 2023-08-05 15:00:0005/08/2023 15:00 | Falkirk | 3 - 0 | Annan | Scottish League One | N/A |
| 2023-07-29 15:00:0029/07/2023 15:00 | Annan | 2 - 3 | Raith | Scottish League Cup | N/A |
| 2023-07-22 15:00:0022/07/2023 15:00 | Annan | 1 - 2 | Albion | Scottish League Cup | N/A |
| 2023-07-18 19:45:0018/07/2023 19:45 | Dunfermline | 4 - 0 | Annan | Scottish League Cup | N/A |
| 2023-07-15 15:00:0015/07/2023 15:00 | Kilmarnock | 3 - 0 | Annan | Scottish League Cup | N/A |
| 2023-07-07 19:45:0007/07/2023 19:45 | Annan | 1 - 2 | Carlisle | Club Friendly | N/A |
| 2023-07-04 19:45:4804/07/2023 19:45 | Annan | 0 - 1 | Morton | Club Friendly | N/A |
| 2023-05-19 19:35:3519/05/2023 19:35 | Clyde | 1 - 2 | Annan | Scottish League One Playoffs | N/A |
| 2023-05-16 19:35:5416/05/2023 19:35 | Annan | 3 - 1 | Clyde | Scottish League One Playoffs | N/A |
| 2023-05-13 15:00:1113/05/2023 15:00 | Dumbarton | 0 - 0 | Annan | Scottish League One Playoffs | N/A |
| 2023-05-09 19:45:4109/05/2023 19:45 | Annan | 6 - 0 | Dumbarton | Scottish League One Playoffs | N/A |
| 2023-05-06 15:00:0006/05/2023 15:00 | Stenhousemuir | 2 - 1 | Annan | Scottish League Two | N/A |
| 2023-04-29 15:00:0029/04/2023 15:00 | Annan | 0 - 0 | Bonnyrigg | Scottish League Two | N/A |
| 2023-04-22 15:00:0022/04/2023 15:00 | Stirling | 3 - 1 | Annan | Scottish League Two | N/A |
| 2023-04-15 15:00:0015/04/2023 15:00 | Annan | 4 - 0 | Albion | Scottish League Two | N/A |
| 2023-04-08 15:00:0008/04/2023 15:00 | Annan | 3 - 1 | Dumbarton | Scottish League Two | N/A |
| 2023-04-01 15:00:0001/04/2023 15:00 | East Fife | 0 - 1 | Annan | Scottish League Two | N/A |
| 2023-03-25 15:00:0025/03/2023 15:00 | Annan | 0 - 0 | Stranraer | Scottish League Two | N/A |
| 2023-03-18 15:00:0018/03/2023 15:00 | Forfar | 2 - 1 | Annan | Scottish League Two | N/A |
| 2023-03-11 15:00:0011/03/2023 15:00 | Annan | 4 - 1 | Elgin | Scottish League Two | N/A |
| 2023-03-04 15:00:0004/03/2023 15:00 | Annan | 2 - 3 | Stenhousemuir | Scottish League Two | N/A |
| 2023-02-25 15:00:0025/02/2023 15:00 | Albion | 0 - 2 | Annan | Scottish League Two | N/A |
| 2023-02-18 15:00:0018/02/2023 15:00 | Annan | 2 - 2 | Stirling | Scottish League Two | N/A |
| 2023-02-11 15:00:0011/02/2023 15:00 | Dumbarton | 2 - 1 | Annan | Scottish League Two | N/A |
| 2023-02-04 15:00:0004/02/2023 15:00 | Bonnyrigg | 1 - 2 | Annan | Scottish League Two | N/A |
| 2023-01-28 15:00:0028/01/2023 15:00 | Annan | 3 - 0 | East Fife | Scottish League Two | N/A |
| 2023-01-21 15:00:0021/01/2023 15:00 | Annan | 4 - 0 | Bonnyrigg | Scottish League Two | N/A |
| 2023-01-14 15:00:0014/01/2023 15:00 | Elgin | 1 - 1 | Annan | Scottish League Two | N/A |
| 2023-01-07 15:00:0007/01/2023 15:00 | Annan | 0 - 2 | Forfar | Scottish League Two | N/A |
| 2022-12-23 19:45:0023/12/2022 19:45 | Annan | 5 - 1 | Albion | Scottish League Two | N/A |
| 2022-12-03 15:00:0003/12/2022 15:00 | East Fife | 1 - 3 | Annan | Scottish League Two | N/A |
| 2022-11-26 15:00:0026/11/2022 15:00 | Stranraer | 1 - 1 | Annan | Scottish League Two | N/A |
| 2022-11-19 15:00:0019/11/2022 15:00 | Annan | 1 - 3 | Elgin | Scottish League Two | N/A |
| 2022-11-12 15:00:0012/11/2022 15:00 | Stirling | 0 - 2 | Annan | Scottish League Two | N/A |
| 2022-11-05 15:00:0005/11/2022 15:00 | Forfar | 1 - 4 | Annan | Scottish League Two | N/A |
| 2022-10-29 15:00:0029/10/2022 15:00 | Annan | 0 - 1 | Dumbarton | Scottish League Two | N/A |
| 2022-10-24 19:45:0024/10/2022 19:45 | Pollok | 4 - 3 | Annan | Scottish Cup | N/A |
| 2022-10-15 15:00:0015/10/2022 15:00 | Annan | 1 - 1 | Stranraer | Scottish League Two | N/A |
| 2022-10-11 19:45:0011/10/2022 19:45 | Bonnyrigg | 2 - 0 | Annan | Scottish League Two | N/A |
| 2022-10-08 15:00:0008/10/2022 15:00 | Stenhousemuir | 2 - 2 | Annan | Scottish League Two | N/A |
| 2022-10-01 15:00:0001/10/2022 15:00 | Elgin | 5 - 1 | Annan | Scottish League Two | N/A |
| 2022-09-23 19:45:0023/09/2022 19:45 | Annan | 1 - 2 | Kelty | Scottish Challenge Cup | N/A |
| 2022-09-17 15:00:0017/09/2022 15:00 | Annan | 2 - 2 | East Fife | Scottish League Two | N/A |
| 2022-09-03 15:00:0003/09/2022 15:00 | Annan | 2 - 1 | Forfar | Scottish League Two | N/A |
| 2022-08-30 19:45:0030/08/2022 19:45 | Annan | 1 - 4 | Aberdeen | Scottish League Cup | N/A |
| 2022-08-27 15:00:0027/08/2022 15:00 | Albion | 2 - 2 | Annan | Scottish League Two | N/A |
| 2022-08-23 19:45:0023/08/2022 19:45 | East Kilbride | 1 (4) - 1 (5) | Annan | Scottish Challenge Cup | N/A |
| 2022-08-20 15:00:0020/08/2022 15:00 | Annan | 1 - 2 | Stirling | Scottish League Two | N/A |
| 2022-08-13 15:00:0013/08/2022 15:00 | Dumbarton | 4 - 0 | Annan | Scottish League Two | N/A |
| 2022-08-06 15:00:0006/08/2022 15:00 | Annan | 2 - 1 | Stenhousemuir | Scottish League Two | N/A |
| 2022-07-30 15:00:0030/07/2022 15:00 | Stranraer | 1 - 0 | Annan | Scottish League Two | N/A |
| 2022-07-19 19:45:0019/07/2022 19:45 | Annan | 1 - 1 | Ayr | Scottish League Cup | N/A |
| 2022-07-16 15:00:0016/07/2022 15:00 | Annan | 4 - 0 | Elgin | Scottish League Cup | N/A |
| 2022-07-12 19:45:0012/07/2022 19:45 | St Johnstone | 0 - 0 | Annan | Scottish League Cup | N/A |
| 2022-07-09 15:00:0009/07/2022 15:00 | QOTS | 2 - 3 | Annan | Scottish League Cup | N/A |
| 2022-07-02 15:00:0002/07/2022 15:00 | Atherton | 2 - 1 | Annan | Club Friendly | N/A |
| 2022-06-25 14:00:1725/06/2022 14:00 | Annan | 2 - 2 | Morton | Club Friendly | N/A |
| 2022-05-13 19:30:5213/05/2022 19:30 | Annan | 2 - 1 | Edinburgh City | Scottish League One Playoffs | N/A |
| 2022-05-10 19:30:1210/05/2022 19:30 | Edinburgh City | 2 - 0 | Annan | Scottish League One Playoffs | N/A |
| 2022-05-07 15:00:0007/05/2022 15:00 | Forfar | 1 - 1 | Annan | Scottish League One Playoffs | N/A |
| 2022-05-03 19:45:0003/05/2022 19:45 | Annan | 1 - 0 | Forfar | Scottish League One Playoffs | N/A |
| 2022-04-30 15:00:0030/04/2022 15:00 | Annan | 1 - 2 | Kelty | Scottish League Two | N/A |
| 2022-04-22 19:45:0022/04/2022 19:45 | Edinburgh City | 2 - 1 | Annan | Scottish League Two | N/A |
| 2022-04-16 15:00:0016/04/2022 15:00 | Forfar | 5 - 1 | Annan | Scottish League Two | N/A |
| 2022-04-09 15:00:0009/04/2022 15:00 | Annan | 2 - 3 | Cowdenbeath | Scottish League Two | N/A |
| 2022-04-02 15:00:0002/04/2022 15:00 | Stenhousemuir | 0 - 1 | Annan | Scottish League Two | N/A |
| 2022-03-26 15:00:0026/03/2022 15:00 | Annan | 2 - 4 | Albion | Scottish League Two | N/A |
| 2022-03-19 15:00:0019/03/2022 15:00 | Stirling | 0 - 3 | Annan | Scottish League Two | N/A |
| 2022-03-12 15:00:0012/03/2022 15:00 | Annan | 2 - 1 | Elgin | Scottish League Two | N/A |
| 2022-03-05 15:00:0005/03/2022 15:00 | Annan | 4 - 1 | Stranraer | Scottish League Two | N/A |
| 2022-03-02 19:45:0002/03/2022 19:45 | Albion | 1 - 4 | Annan | Scottish League Two | N/A |
| 2022-02-26 15:00:0026/02/2022 15:00 | Kelty | 3 - 1 | Annan | Scottish League Two | N/A |
| 2022-02-19 15:00:0019/02/2022 15:00 | Annan | 2 - 1 | Edinburgh City | Scottish League Two | N/A |
| 2022-02-15 19:45:0015/02/2022 19:45 | Elgin | 0 - 2 | Annan | Scottish League Two | N/A |
| 2022-02-12 17:30:0012/02/2022 17:30 | Annan | 0 - 3 | Rangers | Scottish Cup | N/A |
| 2022-02-05 15:00:0005/02/2022 15:00 | Annan | 0 - 2 | Stenhousemuir | Scottish League Two | N/A |
| 2022-01-29 15:45:0029/01/2022 15:45 | Annan | 0 - 0 | Stirling | Scottish League Two | N/A |
| 2022-01-22 15:00:0022/01/2022 15:00 | Clydebank | 3 - 4 | Annan | Scottish Cup | N/A |
| 2022-01-15 15:00:0015/01/2022 15:00 | Annan | 2 - 2 | Forfar | Scottish League Two | N/A |
| 2022-01-08 15:00:0008/01/2022 15:00 | Cowdenbeath | 1 - 3 | Annan | Scottish League Two | N/A |
| 2022-01-02 15:00:0002/01/2022 15:00 | Stranraer | 1 - 1 | Annan | Scottish League Two | N/A |
| 2021-12-26 13:00:0026/12/2021 13:00 | Annan | 5 - 1 | Kelty | Scottish League Two | N/A |
| 2021-12-18 15:00:0018/12/2021 15:00 | Stirling | 2 - 3 | Annan | Scottish League Two | N/A |
| 2021-12-11 15:00:0011/12/2021 15:00 | Annan | 4 - 1 | Elgin | Scottish League Two | N/A |
| 2021-12-03 19:45:0003/12/2021 19:45 | Edinburgh City | 0 - 1 | Annan | Scottish League Two | N/A |
| 2021-11-27 15:00:0027/11/2021 15:00 | Gala Fairydean | 0 - 1 | Annan | Scottish Cup | N/A |
| 2021-11-20 15:00:0020/11/2021 15:00 | Annan | 1 - 1 | Albion | Scottish League Two | N/A |
| 2021-11-13 15:00:0013/11/2021 15:00 | Stenhousemuir | 2 - 0 | Annan | Scottish League Two | N/A |
| 2021-11-06 15:00:0006/11/2021 15:00 | Annan | 2 - 2 | Stranraer | Scottish League Two | N/A |
| 2021-10-30 15:00:0030/10/2021 15:00 | Annan | 1 - 0 | Cowdenbeath | Scottish League Two | N/A |
| 2021-10-23 15:00:0023/10/2021 15:00 | Annan | 3 - 1 | Jeanfield | Scottish Cup | N/A |
| 2021-10-16 15:00:0016/10/2021 15:00 | Forfar | 2 - 0 | Annan | Scottish League Two | N/A |
| 2021-10-02 15:00:0002/10/2021 15:00 | Kelty | 2 - 1 | Annan | Scottish League Two | N/A |
| 2021-09-25 15:00:0025/09/2021 15:00 | Annan | 1 - 3 | Edinburgh City | Scottish League Two | N/A |
| 2021-09-18 15:00:0018/09/2021 15:00 | Elgin | 0 - 2 | Annan | Scottish League Two | N/A |
| 2021-09-11 15:00:0011/09/2021 15:00 | Annan | 1 - 2 | Stenhousemuir | Scottish League Two | N/A |
| 2021-08-28 15:00:0028/08/2021 15:00 | Cowdenbeath | 1 - 3 | Annan | Scottish League Two | N/A |
| 2021-08-21 15:00:0021/08/2021 15:00 | Albion | 0 - 1 | Annan | Scottish League Two | N/A |
| 2021-08-14 15:00:0014/08/2021 15:00 | Annan | 3 - 1 | Stirling | Scottish League Two | N/A |
| 2021-08-11 19:45:0011/08/2021 19:45 | Celtic U20 | 2 - 0 | Annan | Scottish Challenge Cup | N/A |
| 2021-08-07 15:00:0007/08/2021 15:00 | Stranraer | 0 - 3 | Annan | Scottish League Two | N/A |
| 2021-07-31 15:00:0031/07/2021 15:00 | Annan | 0 - 2 | Forfar | Scottish League Two | N/A |
| 2021-07-24 15:00:0024/07/2021 15:00 | Motherwell | 2 - 0 | Annan | Scottish League Cup | N/A |
| 2021-07-20 19:45:0020/07/2021 19:45 | Annan | 1 - 2 | Queen’s Park | Scottish League Cup | N/A |
| 2021-07-13 19:45:0013/07/2021 19:45 | Annan | 1 - 3 | QOTS | Scottish League Cup | N/A |
| 2021-07-10 15:00:0010/07/2021 15:00 | Airdrieonians | 1 - 1 | Annan | Scottish League Cup | N/A |
| 2021-05-01 15:00:0001/05/2021 15:00 | Annan | 1 - 1 | Cowdenbeath | Scottish League Two | N/A |
| 2021-04-29 19:00:0029/04/2021 19:00 | Brechin | 0 - 3 | Annan | Scottish League Two | N/A |
| 2021-04-27 19:00:0027/04/2021 19:00 | Annan | 1 - 1 | Stenhousemuir | Scottish League Two | N/A |
| 2021-04-24 15:00:0024/04/2021 15:00 | Albion | 1 - 0 | Annan | Scottish League Two | N/A |
| 2021-04-20 19:45:0020/04/2021 19:45 | Annan | 5 - 1 | Stenhousemuir | Scottish League Two | N/A |
| 2021-04-17 12:00:0017/04/2021 12:00 | Annan | 3 - 0 | Brechin | Scottish League Two | N/A |
| 2021-04-13 19:00:0013/04/2021 19:00 | Queen’s Park | 1 - 0 | Annan | Scottish League Two | N/A |
| 2021-04-10 15:00:0010/04/2021 15:00 | Annan | 1 - 2 | Stirling | Scottish League Two | N/A |
| 2021-04-06 19:00:0006/04/2021 19:00 | Edinburgh City | 1 - 1 | Annan | Scottish League Two | N/A |
| 2021-04-03 15:00:0003/04/2021 15:00 | Annan | 0 - 3 | Elgin | Scottish League Two | N/A |
| 2021-03-27 15:00:0027/03/2021 15:00 | Albion | 1 - 1 | Annan | Scottish League Two | N/A |
| 2021-03-23 19:45:0023/03/2021 19:45 | Formartine | 1 (3) - 1 (1) | Annan | Scottish Cup | N/A |
| 2021-03-20 15:00:0020/03/2021 15:00 | Annan | 0 - 0 | Cowdenbeath | Scottish League Two | N/A |
| 2021-01-02 15:00:0002/01/2021 15:00 | Stranraer | 2 - 0 | Annan | Scottish League Two | N/A |
| 2020-12-26 15:00:0026/12/2020 15:00 | Gala Fairydean | 1 - 2 | Annan | Scottish Cup | N/A |
| 2020-12-22 19:45:0022/12/2020 19:45 | Brechin | 0 - 0 | Annan | Scottish League Two | N/A |
| 2020-12-19 15:00:0019/12/2020 15:00 | Annan | 1 - 2 | Queen’s Park | Scottish League Two | N/A |
| 2020-12-05 15:00:0005/12/2020 15:00 | Elgin | 1 - 0 | Annan | Scottish League Two | N/A |
| 2020-11-28 15:00:0028/11/2020 15:00 | Annan | 0 - 4 | Edinburgh City | Scottish League Two | N/A |
| 2020-11-21 15:00:0021/11/2020 15:00 | Stenhousemuir | 1 - 2 | Annan | Scottish League Two | N/A |
| 2020-11-10 19:45:0010/11/2020 19:45 | Albion | 1 - 5 | Annan | Scottish League Cup | N/A |
| 2020-11-07 15:00:0007/11/2020 15:00 | Annan | 2 - 3 | Albion | Scottish League Two | N/A |
| 2020-10-31 15:00:0031/10/2020 15:00 | Stirling | 1 - 0 | Annan | Scottish League Two | N/A |
| 2020-10-24 15:00:0024/10/2020 15:00 | Annan | 1 - 1 | Stranraer | Scottish League Two | N/A |
| 2020-10-17 15:00:0017/10/2020 15:00 | Cowdenbeath | 0 - 3 | Annan | Scottish League Two | N/A |
| 2020-10-13 19:45:0013/10/2020 19:45 | Ayr | 1 - 0 | Annan | Scottish League Cup | N/A |
| 2020-10-10 15:00:0010/10/2020 15:00 | Annan | 1 - 1 | Stranraer | Scottish League Cup | N/A |
| 2020-10-06 19:45:0006/10/2020 19:45 | Annan | 3 - 1 | Hamilton | Scottish League Cup | N/A |
| 2020-03-07 15:00:0007/03/2020 15:00 | Annan | 0 - 0 | Cowdenbeath | Scottish League Two | N/A |
| 2020-02-29 15:00:0029/02/2020 15:00 | Queen’s Park | 2 - 0 | Annan | Scottish League Two | N/A |
| 2020-02-22 15:00:0022/02/2020 15:00 | Annan | 2 - 1 | Albion | Scottish League Two | N/A |
| 2020-02-08 15:00:0008/02/2020 15:00 | Edinburgh City | 3 - 0 | Annan | Scottish League Two | N/A |
| 2020-02-01 15:00:0001/02/2020 15:00 | Annan | 0 - 3 | Stenhousemuir | Scottish League Two | N/A |
| 2020-01-25 15:00:0025/01/2020 15:00 | Cove | 2 - 0 | Annan | Scottish League Two | N/A |
| 2020-01-18 15:00:0018/01/2020 15:00 | Annan | 2 - 3 | Stirling | Scottish League Two | N/A |
| 2020-01-11 15:00:0011/01/2020 15:00 | Annan | 0 - 4 | Elgin | Scottish League Two | N/A |
| 2020-01-04 15:00:0004/01/2020 15:00 | Cowdenbeath | 3 - 1 | Annan | Scottish League Two | N/A |
| 2019-12-28 15:00:0028/12/2019 15:00 | Annan | 3 - 2 | Queen’s Park | Scottish League Two | N/A |
| 2019-12-21 15:00:0021/12/2019 15:00 | Albion | 4 - 2 | Annan | Scottish League Two | N/A |
| 2019-12-14 15:00:0014/12/2019 15:00 | Annan | 0 - 2 | Edinburgh City | Scottish League Two | N/A |
| 2019-12-07 15:00:0007/12/2019 15:00 | Stenhousemuir | 1 - 2 | Annan | Scottish League Two | N/A |
| 2019-11-30 15:00:0030/11/2019 15:00 | Annan | 6 - 1 | Cove | Scottish League Two | N/A |
| 2019-11-23 15:00:0023/11/2019 15:00 | Edinburgh City | 4 - 3 | Annan | Scottish Cup | N/A |
| 2019-11-16 15:00:0016/11/2019 15:00 | Stirling | 2 - 0 | Annan | Scottish League Two | N/A |
| 2019-11-12 19:45:0012/11/2019 19:45 | Annan | 5 - 2 | Brechin | Scottish League Two | N/A |
| 2019-11-09 15:00:0009/11/2019 15:00 | Annan | 1 - 0 | Cowdenbeath | Scottish League Two | N/A |
| 2019-11-02 15:00:0002/11/2019 15:00 | Elgin | 4 - 0 | Annan | Scottish League Two | N/A |
| 2019-10-26 15:00:0026/10/2019 15:00 | Brechin | 0 - 2 | Annan | Scottish Cup | N/A |
| 2019-10-19 15:00:0019/10/2019 15:00 | Annan | 2 - 2 | Brechin | Scottish Cup | N/A |
| 2019-10-05 15:00:0005/10/2019 15:00 | Queen’s Park | 1 - 2 | Annan | Scottish League Two | N/A |
| 2019-09-28 15:00:0028/09/2019 15:00 | Cove | 3 - 0 | Annan | Scottish League Two | N/A |
| 2019-09-21 15:00:0021/09/2019 15:00 | Annan | 0 - 0 | Stirling | Scottish League Two | N/A |
| 2019-09-14 15:00:0014/09/2019 15:00 | Edinburgh City | 4 - 0 | Annan | Scottish League Two | N/A |
| 2019-08-31 15:00:0031/08/2019 15:00 | Annan | 1 - 1 | Stenhousemuir | Scottish League Two | N/A |
| 2019-08-24 15:00:0024/08/2019 15:00 | Cowdenbeath | 3 - 1 | Annan | Scottish League Two | N/A |
| 2019-08-17 15:00:0017/08/2019 15:00 | Annan | 3 - 2 | Albion | Scottish League Two | N/A |
| 2019-08-13 19:45:0013/08/2019 19:45 | Annan | 1 (5) - 1 (6) | Kelty | Scottish Challenge Cup | N/A |
| 2019-08-10 15:00:0010/08/2019 15:00 | Annan | 1 - 1 | Elgin | Scottish League Two | N/A |
| 2019-08-03 15:00:0003/08/2019 15:00 | Brechin | 0 - 1 | Annan | Scottish League Two | N/A |
| 2019-07-27 15:00:0027/07/2019 15:00 | Motherwell | 4 - 0 | Annan | Scottish League Cup | N/A |
| 2019-07-23 19:45:0023/07/2019 19:45 | Annan | 0 - 5 | Morton | Scottish League Cup | N/A |
| 2019-07-16 19:45:0016/07/2019 19:45 | QOTS | 3 - 3 | Annan | Scottish League Cup | N/A |
| 2019-07-13 15:00:0013/07/2019 15:00 | Annan | 0 - 1 | Dumbarton | Scottish League Cup | N/A |
| 2019-07-06 14:00:0006/07/2019 14:00 | Linlithgow | 1 - 1 | Annan | Club Friendly | N/A |
| 2019-06-27 19:45:0027/06/2019 19:45 | Stranraer | 0 - 1 | Annan | Club Friendly | N/A |
| 2019-05-18 15:00:0018/05/2019 15:00 | Clyde | 2 - 0 | Annan | Scottish League One Playoffs | N/A |
| 2019-05-14 19:45:0014/05/2019 19:45 | Annan | 1 - 0 | Clyde | Scottish League One Playoffs | N/A |
| 2019-05-11 15:00:0011/05/2019 15:00 | Stenhousemuir | 1 - 2 | Annan | Scottish League One Playoffs | N/A |
| 2019-05-07 19:45:0007/05/2019 19:45 | Annan | 2 - 0 | Stenhousemuir | Scottish League One Playoffs | N/A |
| 2019-05-04 15:00:0004/05/2019 15:00 | Albion | 0 - 2 | Annan | Scottish League Two | N/A |
| 2019-04-27 15:00:1627/04/2019 15:00 | Annan | 3 - 2 | Cowdenbeath | Scottish League Two | N/A |
| 2019-04-20 15:00:0020/04/2019 15:00 | Queen’s Park | 0 - 3 | Annan | Scottish League Two | N/A |
| 2019-04-13 15:00:0013/04/2019 15:00 | Annan | 2 - 2 | Stirling | Scottish League Two | N/A |
| 2019-04-06 15:00:0006/04/2019 15:00 | Annan | 6 - 0 | Berwick | Scottish League Two | N/A |
| 2019-03-30 15:00:0030/03/2019 15:00 | Elgin | 0 - 1 | Annan | Scottish League Two | N/A |
| 2019-03-23 15:00:0023/03/2019 15:00 | Clyde | 2 - 1 | Annan | Scottish League Two | N/A |
| 2019-03-16 15:00:0016/03/2019 15:00 | Annan | 3 - 1 | Edinburgh City | Scottish League Two | N/A |
| 2019-03-09 15:00:0009/03/2019 15:00 | Peterhead | 2 - 1 | Annan | Scottish League Two | N/A |
| 2019-03-02 15:00:0002/03/2019 15:00 | Annan | 2 - 1 | Queen’s Park | Scottish League Two | N/A |
| 2019-02-26 19:45:0026/02/2019 19:45 | Berwick | 1 - 2 | Annan | Scottish League Two | N/A |
| 2019-02-23 15:00:0023/02/2019 15:00 | Annan | 4 - 0 | Albion | Scottish League Two | N/A |
| 2019-02-16 15:00:0016/02/2019 15:00 | Cowdenbeath | 2 - 4 | Annan | Scottish League Two | N/A |
| 2019-02-09 15:00:0009/02/2019 15:00 | Annan | 1 - 1 | Clyde | Scottish League Two | N/A |
| 2019-01-26 15:00:0026/01/2019 15:00 | Annan | 3 - 0 | Peterhead | Scottish League Two | N/A |
| 2019-01-19 15:00:0019/01/2019 15:00 | Edinburgh City | 1 - 2 | Annan | Scottish League Two | N/A |
| 2019-01-12 15:00:0012/01/2019 15:00 | Stirling | 2 - 1 | Annan | Scottish League Two | N/A |
| 2019-01-05 15:00:0005/01/2019 15:00 | Annan | 2 - 0 | Elgin | Scottish League Two | N/A |
| 2018-12-29 15:00:0029/12/2018 15:00 | Albion | 1 - 1 | Annan | Scottish League Two | N/A |
| 2018-12-22 15:00:0022/12/2018 15:00 | Annan | 4 - 0 | Berwick | Scottish League Two | N/A |
| 2018-12-15 15:00:0015/12/2018 15:00 | Clyde | 1 - 0 | Annan | Scottish League Two | N/A |
| 2018-12-08 15:00:0008/12/2018 15:00 | Annan | 1 - 2 | Edinburgh City | Scottish League Two | N/A |
| 2018-12-01 15:00:0001/12/2018 15:00 | Peterhead | 2 - 1 | Annan | Scottish League Two | N/A |
| 2018-11-27 19:45:0027/11/2018 19:45 | Annan | 3 - 4 | Montrose | Scottish Cup | N/A |
| 2018-11-24 15:00:0024/11/2018 15:00 | Montrose | 0 - 0 | Annan | Scottish Cup | N/A |
| 2018-11-17 15:00:0017/11/2018 15:00 | Annan | 2 - 2 | Stirling | Scottish League Two | N/A |
| 2018-11-10 15:00:0010/11/2018 15:00 | Annan | 0 - 2 | Cowdenbeath | Scottish League Two | N/A |
| 2018-11-03 15:00:0003/11/2018 15:00 | Queen’s Park | 0 - 0 | Annan | Scottish League Two | N/A |
| 2018-10-27 15:00:0027/10/2018 15:00 | Elgin | 0 - 1 | Annan | Scottish League Two | N/A |
| 2018-10-20 15:00:0020/10/2018 15:00 | Rothes | 0 - 1 | Annan | Scottish Cup | N/A |
| 2018-10-06 15:00:0006/10/2018 15:00 | Annan | 3 - 1 | Albion | Scottish League Two | N/A |
| 2018-09-29 15:00:5929/09/2018 15:00 | Annan | 1 - 3 | Peterhead | Scottish League Two | N/A |
| 2018-09-22 15:00:0522/09/2018 15:00 | Stirling | 1 - 2 | Annan | Scottish League Two | N/A |
| 2018-09-15 15:00:4415/09/2018 15:00 | Edinburgh City | 2 - 1 | Annan | Scottish League Two | N/A |
| 2018-09-08 15:00:3308/09/2018 15:00 | Arbroath | 3 - 0 | Annan | Scottish Challenge Cup | N/A |
| 2018-09-01 15:00:5501/09/2018 15:00 | Annan | 1 - 2 | Clyde | Scottish League Two | N/A |
| 2018-08-25 15:00:1725/08/2018 15:00 | Berwick | 0 - 3 | Annan | Scottish League Two | N/A |
| 2018-08-18 15:00:1918/08/2018 15:00 | Annan | 3 - 1 | Queen’s Park | Scottish League Two | N/A |
| 2018-08-14 19:45:3714/08/2018 19:45 | Annan | 4 - 0 | Celtic U20 | Scottish Challenge Cup | N/A |
| 2018-08-11 15:00:2511/08/2018 15:00 | Cowdenbeath | 1 - 2 | Annan | Scottish League Two | N/A |
| 2018-08-04 15:00:1404/08/2018 15:00 | Annan | 1 - 1 | Elgin | Scottish League Two | N/A |
| 2018-07-24 19:45:2824/07/2018 19:45 | Airdrieonians | 4 - 1 | Annan | Scottish League Cup | N/A |
| 2018-07-21 15:00:2521/07/2018 15:00 | Livingston | 1 - 0 | Annan | Scottish League Cup | N/A |
| 2018-07-17 19:45:2017/07/2018 19:45 | Annan | 4 - 0 | Berwick | Scottish League Cup | N/A |
| 2018-07-14 15:00:4314/07/2018 15:00 | Annan | 1 - 0 | Hamilton | Scottish League Cup | N/A |
| 2018-06-30 14:00:0730/06/2018 14:00 | Annan | 2 - 2 | QOTS | Club Friendly | N/A |
