| Championship | 05/10/19 | Dundee FC | - | Arbroath FC | 2:0 | ||||
| Championship | 16/11/19 | Greenock Morton FC | - | Arbroath FC | 1:0 | ||||
| Championship | 07/12/19 | Arbroath FC | - | Dundee FC | 1:1 | ||||
| Championship | 03/02/21 | Arbroath FC | - | Inverness CT | 1:1 | ||||
| League Cup | 21/07/21 | Montrose FC | - | Dundee FC | 0:2 | ||||
| League One | 18/09/21 | Montrose FC | - | Alloa Athletic | 0:2 | ||||
| Playoffs | 07/05/22 | Airdrieonians FC | - | Montrose FC | 6:4 aet | ||||
| League Cup | 19/07/22 | Montrose FC | - | Stenhousemuir FC | 0:2 | ||||
| League One | 04/10/22 | Montrose FC | - | Airdrieonians FC | 4:2 |
Scotland