Head to Head
| 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 |
| Scotland League Two | 2018/03/13 19:45 | Montrose v Annan Athletic | L | 2-1 |
| Scotland League Two | 2018/01/06 15:00 | Annan Athletic v Montrose | L | 0-1 |
| Scotland League Two | 2017/11/11 15:00 | Montrose v Annan Athletic | D | 1-1 |
| Scotland League Two | 2017/08/26 14:00 | Annan Athletic v Montrose | L | 0-1 |
Home History
| Scotland League One | 2023/12/30 15:00 | Queen of South v Annan Athletic | L | 2-1 |
| Scotland League One | 2023/12/23 15:00 | Annan Athletic v Falkirk | L | 0-3 |
| Scotland League One | 2023/12/16 15:00 | Stirling v Annan Athletic | D | 1-1 |
| Scotland League One | 2023/12/09 15:00 | Annan Athletic v Cove Rangers | L | 1-3 |
| Scotland League One | 2023/11/28 19:45 | Annan Athletic v Hamilton | L | 1-2 |
| Scotland FA Cup | 2023/11/25 15:00 | Annan Athletic v Dumbarton | L | 4-5 |
| Scotland League One | 2023/11/11 15:00 | Montrose v Annan Athletic | D | 1-1 |
| Scotland League One | 2023/11/04 15:00 | Annan Athletic v Kelty Hearts | D | 2-2 |
Away History
| Scotland League One | 2023/12/30 15:00 | Montrose v Cove Rangers | D | 1-1 |
| Scotland League One | 2023/12/23 15:00 | Alloa v Montrose | D | 2-2 |
| Scotland League One | 2023/12/16 15:00 | Kelty Hearts v Montrose | W | 0-1 |
| Scotland League One | 2023/12/09 15:00 | Montrose v Queen of South | L | 1-4 |
| Scotland League One | 2023/11/28 19:45 | Montrose v Falkirk | D | 0-0 |
| Scotland FA Cup | 2023/11/25 15:00 | Montrose v FC Edinburgh | W | 3-0 |
| Scotland League One | 2023/11/14 19:45 | Cove Rangers v Montrose | L | 1-0 |
| Scotland League One | 2023/11/11 15:00 | Montrose v Annan Athletic | D | 1-1 |