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 |
Home History
| UK Friendlies | 2024/07/03 18:45 | Montrose v Raith | L | 0-1 |
| Europe Friendlies | 2024/06/29 14:00 | Turriff United v Montrose | D | 1-1 |
| Scotland Championship Play-Offs | 2024/05/11 14:00 | Inverness CT v Montrose | L | 1-0 |
| Scotland Championship Play-Offs | 2024/05/07 18:45 | Montrose v Inverness CT | D | 0-0 |
| Scotland League One | 2024/05/04 14:00 | Montrose v Queen of South | W | 3-2 |
| Scotland League One | 2024/04/27 14:00 | Kelty Hearts v Montrose | W | 0-2 |
| Scotland League One | 2024/04/20 14:00 | Montrose v Hamilton | L | 1-2 |
| Scotland League One | 2024/04/16 18:45 | FC Edinburgh v Montrose | L | 1-0 |
Away History
| Europe Friendlies | 2024/07/02 19:00 | Gretna 2008 v Annan Athletic | W | 0-3 |
| Europe Friendlies | 2024/06/29 12:00 | Dundee Utd v Annan Athletic | L | 2-0 |
| Scotland League One | 2024/05/04 14:00 | Stirling v Annan Athletic | D | 1-1 |
| Scotland League One | 2024/04/27 14:00 | Annan Athletic v Falkirk | D | 3-3 |
| Scotland League One | 2024/04/20 14:00 | FC Edinburgh v Annan Athletic | W | 1-2 |
| Scotland League One | 2024/04/13 14:00 | Annan Athletic v Cove Rangers | W | 4-2 |
| Scotland League One | 2024/04/06 14:00 | Annan Athletic v Hamilton | L | 1-3 |
| Scotland League One | 2024/03/30 15:00 | Alloa v Annan Athletic | D | 1-1 |