Home History
| Scotland League Cup | 2023/07/22 14:00 | Annan Athletic v Albion | L | 1-2 |
| Scotland League Cup | 2023/07/18 18:45 | Dunfermline v Annan Athletic | L | 4-0 |
| Scotland League Cup | 2023/07/15 14:00 | Kilmarnock v Annan Athletic | L | 3-0 |
| Scotland League One Play-Offs | 2023/05/19 18:35 | Clyde v Annan Athletic | W | 1-2 |
| Scotland League One Play-Offs | 2023/05/16 18:35 | Annan Athletic v Clyde | W | 3-1 |
| Scotland League One Play-Offs | 2023/05/13 14:00 | Dumbarton v Annan Athletic | D | 0-0 |
| Scotland League One Play-Offs | 2023/05/09 18:45 | Annan Athletic v Dumbarton | W | 6-0 |
| Scotland League Two | 2023/05/06 14:00 | Stenhousemuir v Annan Athletic | L | 2-1 |
Away History
| Scotland League Cup | 2023/07/26 18:45 | Kilmarnock v Raith | D | 2-2 |
| Scotland League Cup | 2023/07/18 18:45 | Raith v Albion | W | 2-0 |
| Scotland League Cup | 2023/07/15 16:15 | Raith v Dunfermline | D | 1-1 |
| Club Friendly List | 2023/07/08 13:00 | East Fife v Raith | W | 0-2 |
| Club Friendly List | 2023/07/01 13:00 | Kelty Hearts v Raith | W | 3-6 |
| Club Friendly List | 2023/06/27 18:45 | Montrose v Raith | W | 1-3 |
| Club Friendly List | 2023/06/24 13:30 | Linlithgow Rose v Raith | W | 1-4 |
| Scotland Championship | 2023/05/05 18:45 | Raith v Partick | D | 2-2 |