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 |
|---|---|---|---|---|
| 2022-01-15 | Scottish Division Two | Annan Athletic | 2 : 2 | Forfar Athletic |
| 2022-01-08 | Scottish Division Two | Cowdenbeath | 1 : 3 | Annan Athletic |
| 2022-01-02 | Scottish Division Two | Stranraer | 1 : 1 | Annan Athletic |
| 2021-12-26 | Scottish Division Two | Annan Athletic | 5 : 1 | Kelty Hearts |
| 2021-12-18 | Scottish Division Two | Stirling Albion | 2 : 3 | Annan Athletic |
| 2021-12-11 | Scottish Division Two | Annan Athletic | 4 : 1 | Elgin City |
| 2021-12-04 | Scottish Division Two | Edinburgh City | 0 : 1 | Annan Athletic |
| 2021-11-27 | Scotland FA Cup | Gala Fairydean | 0 : 1 | Annan Athletic |
| 2021-11-20 | Scottish Division Two | Annan Athletic | 1 : 1 | Albion Rovers |
| 2021-11-13 | Scottish Division Two | Stenhousemuir | 2 : 0 | Annan Athletic |
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