| League One | 12/08/23 | Annan Athletic | - | Montrose FC | 1:3 |  |
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| League One | 06/01/24 | Annan Athletic | - | Montrose FC | 2:2 | ||||
| League One | 16/03/24 | Montrose FC | - | Annan Athletic | 1:1 | ||||
| League One | 05/10/24 | Annan Athletic | - | Montrose FC | 1:0 | |
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| League One | 23/11/24 | Montrose FC | - | Annan Athletic | 2:1 | |
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| League One | 25/01/25 | Annan Athletic | - | Montrose FC | 2:2 | ||||
| League One | 22/03/25 | Montrose FC | - | Annan Athletic | 3:1 |
Ireland