Head to Head
| Scotland League Cup | 2014/08/02 14:00 | Dunfermline v Annan Athletic | W | 5-1 |
Home History
| Scotland League Cup | 2023/07/15 16:15 | Raith v Dunfermline | D | 1-1 |
| Club Friendly List | 2023/07/11 18:30 | Alloa v Dunfermline | W | 0-1 |
| Club Friendly List | 2023/07/09 14:00 | Dunfermline v Hearts | D | 1-1 |
| Club Friendly List | 2023/07/04 18:45 | Dunfermline v St Johnstone | D | 1-1 |
| Club Friendly List | 2023/06/28 18:30 | Cove Rangers v Dunfermline | D | 1-1 |
| Europe Friendlies | 2023/06/23 18:00 | Dunfermline v St Pauli | L | 0-3 |
| Scotland League One | 2023/05/06 14:00 | Alloa v Dunfermline | W | 0-2 |
| Scotland League One | 2023/04/29 14:00 | Dunfermline v Clyde | W | 2-1 |
Away History
| 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 |
| Scotland League Two | 2023/04/29 14:00 | Annan Athletic v Bonnyrigg Rose | D | 0-0 |
| Scotland League Two | 2023/04/22 14:00 | Stirling v Annan Athletic | L | 3-1 |