Head to Head
| 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 |
Home History
| Scotland League Two | 2016/08/20 14:00 | Stirling v Montrose | L | 2-0 |
| Scotland League Challenge Cup | 2016/08/17 18:45 | Turriff United v Montrose | L | 1-0 |
| Scotland League Two | 2016/08/13 14:00 | Montrose v Arbroath | D | 1-1 |
| Scotland League Two | 2016/08/06 14:00 | Clyde v Montrose | L | 2-1 |
| Scotland League Challenge Cup | 2016/08/02 18:45 | East Stirlingshire v Montrose | W | 0-3 |
| Scotland League Cup | 2016/07/27 18:45 | Cove Rangers v Montrose | L | 3-0 |
| Scotland League Cup | 2016/07/23 14:00 | Montrose v Alloa | L | 0-2 |
| Scotland League Cup | 2016/07/19 18:45 | Raith v Montrose | L | 2-1 |
Away History
| Scotland League Two | 2016/08/20 14:00 | Annan Athletic v Clyde | W | 3-2 |
| Scotland League Two | 2016/08/13 14:00 | Berwick Rangers v Annan Athletic | L | 2-0 |
| Scotland League Two | 2016/08/06 14:00 | Annan Athletic v Stirling | W | 3-2 |
| Scotland League Challenge Cup | 2016/08/02 18:45 | Celtic U20 v Annan Athletic | L | 5-1 |
| Scotland League Cup | 2016/07/30 14:00 | East Stirlingshire v Annan Athletic | W | 0-2 |
| Scotland League Cup | 2016/07/23 14:00 | Annan Athletic v Motherwell | L | 1-3 |
| Scotland League Cup | 2016/07/19 18:45 | Rangers v Annan Athletic | L | 2-0 |
| Scotland League Cup | 2016/07/16 14:00 | Annan Athletic v Stranraer | L | 1-2 |