Head to Head
| 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 | W | 1-3 |
| Scotland FA Cup | 2018/11/27 19:45 | Annan Athletic v Montrose | W | 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 | W | 2-1 |
| Scotland League Two | 2018/01/06 15:00 | Annan Athletic v Montrose | W | 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 | W | 0-1 |
| Scotland League Two | 2017/04/29 14:00 | Annan Athletic v Montrose | L | 5-1 |
| Scotland League Two | 2017/03/04 15:00 | Montrose v Annan Athletic | L | 2-3 |
| Scotland League Two | 2016/11/08 19:45 | Annan Athletic v Montrose | W | 2-3 |
| Scotland League Two | 2016/08/27 14:00 | Montrose v Annan Athletic | D | 2-2 |
| Scotland League Two | 2016/03/26 15:00 | Montrose v Annan Athletic | L | 0-5 |
| Scotland League Two | 2016/02/13 15:00 | Annan Athletic v Montrose | D | 3-3 |
| Scotland League Two | 2015/12/15 19:45 | Montrose v Annan Athletic | D | 1-1 |
| Scotland League Two | 2015/08/29 14:00 | Annan Athletic v Montrose | L | 3-2 |
| Scotland League Two | 2015/05/02 14:00 | Annan Athletic v Montrose | L | 4-3 |
| Scotland League Two | 2015/01/31 15:00 | Montrose v Annan Athletic | W | 2-1 |
| Scotland League Two | 2014/11/15 15:00 | Annan Athletic v Montrose | D | 2-2 |
| Scotland League Two | 2014/08/23 14:00 | Montrose v Annan Athletic | W | 2-0 |