Head to Head
| 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 |
| Scotland League Two | 2017/04/29 14:00 | Annan Athletic v Montrose | W | 5-1 |
| Scotland League Two | 2017/03/04 15:00 | Montrose v Annan Athletic | W | 2-3 |
Home History
| Scotland League One | 2023/08/05 14:00 | Falkirk v Annan Athletic | L | 3-0 |
| Scotland League Cup | 2023/07/29 14:00 | Annan Athletic v Raith | L | 2-3 |
| 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 |
Away History
| Scotland League One | 2023/08/05 14:00 | Montrose v Kelty Hearts | L | 0-2 |
| Scotland League Cup | 2023/07/29 14:00 | Arbroath v Montrose | L | 3-0 |
| Scotland League Cup | 2023/07/22 14:00 | Cowdenbeath v Montrose | W | 5-6 |
| Scotland League Cup | 2023/07/18 18:45 | Montrose v Forfar | L | 1-2 |
| Scotland League Cup | 2023/07/15 14:00 | Montrose v St Mirren | W | 1-0 |
| Club Friendly List | 2023/07/01 13:00 | Arbroath v Montrose | W | 1-3 |
| Club Friendly List | 2023/06/30 18:45 | Montrose v Forfar | L | 1-3 |
| Club Friendly List | 2023/06/27 18:45 | Montrose v Raith | L | 1-3 |