Summary of previous matches between the team of Montrose and the team of Annan Athletic since 2008-08-23:
Montrose won 14 matches against Annan Athletic, lost 18 matches, and 18 matches were draws.
| Time | League | Home Team | Score | Away Team |
|---|---|---|---|---|
| 2019-08-24 | Scottish Division Two | Cowdenbeath | 3 : 1 | Annan Athletic |
| 2019-08-17 | Scottish Division Two | Annan Athletic | 3 : 2 | Albion Rovers |
| 2019-08-14 | Scotland Bells Challenge Cup | Annan Athletic | 1 : 1 | Kelty Hearts |
| 2019-08-10 | Scottish Division Two | Annan Athletic | 1 : 1 | Elgin City |
| 2019-08-03 | Scottish Division Two | Brechin City | 0 : 1 | Annan Athletic |
| 2019-07-07 | International Club Friendly | Linlithgow Rose | 1 : 1 | Annan Athletic |
| 2019-06-28 | International Club Friendly | Annan Athletic | 1 : 0 | Stranraer |
| 2019-05-04 | Scottish Division Two | Albion Rovers | 0 : 2 | Annan Athletic |
| 2019-04-27 | Scottish Division Two | Annan Athletic | 3 : 2 | Cowdenbeath |
| 2019-04-20 | Scottish Division Two | Queen"s Park | 0 : 3 | Annan Athletic |
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