Head to Head
| Scotland League One | 2024/11/23 16:00 | Montrose v Annan Athletic | L | 2-1 |
| Scotland League One | 2024/10/05 14:00 | Annan Athletic v Montrose | W | 1-0 |
| Scotland League One | 2024/03/16 15:00 | Montrose v Annan Athletic | D | 1-1 |
| Scotland League One | 2024/01/06 15:00 | Annan Athletic v Montrose | D | 2-2 |
| Scotland League One | 2023/11/11 15:00 | Montrose v Annan Athletic | D | 1-1 |
| Scotland League One | 2023/08/12 14:00 | Annan Athletic v Montrose | L | 1-3 |
| Scotland FA Cup | 2018/11/27 19:45 | Annan Athletic v Montrose | L | 3-4 |
| Scotland FA Cup | 2018/11/24 15:00 | Montrose v Annan Athletic | D | 0-0 |
Home History
| Scotland League One | 2024/12/21 15:00 | Annan Athletic v Arbroath | L | 0-4 |
| Scotland League One | 2024/12/14 15:00 | Dumbarton v Annan Athletic | W | 1-5 |
| Scotland League One | 2024/12/07 15:00 | Annan Athletic v Cove Rangers | D | 1-1 |
| Scotland FA Cup | 2024/11/30 15:00 | Fraserburgh v Annan Athletic | L | 2-0 |
| Scotland League One | 2024/11/23 16:00 | Montrose v Annan Athletic | L | 2-1 |
| Scotland League One | 2024/11/16 15:00 | Annan Athletic v Kelty Hearts | L | 0-2 |
| Scotland League One | 2024/11/09 15:00 | Annan Athletic v Stenhousemuir | D | 1-1 |
| Scotland League One | 2024/11/02 15:00 | Alloa v Annan Athletic | L | 5-0 |
Away History
| Scotland League One | 2024/12/21 15:00 | Montrose v Dumbarton | L | 1-2 |
| Scotland League One | 2024/12/14 15:00 | Alloa v Montrose | W | 1-2 |
| Scotland League One | 2024/12/07 15:00 | Montrose v Inverness CT | L | 2-3 |
| Scotland FA Cup | 2024/11/30 15:00 | Peterhead v Montrose | W | 2-3 |
| Scotland League One | 2024/11/23 16:00 | Montrose v Annan Athletic | W | 2-1 |
| Scotland League One | 2024/11/16 15:00 | Stenhousemuir v Montrose | L | 1-0 |
| Scotland League One | 2024/11/09 15:00 | Montrose v Arbroath | D | 1-1 |
| Scotland League One | 2024/11/02 15:00 | Queen of South v Montrose | L | 1-0 |