| League Cup | 13.07.19 | Raith Rovers | - | Dundee FC | 0:3 | ||||
| Championship | 31.10.20 | Dundee FC | - | Raith Rovers | 1:1 | ||||
| Championship | 30.01.21 | Raith Rovers | - | Dundee FC | 3:1 | ||||
| Championship | 24.04.21 | Dundee FC | - | Raith Rovers | 2:1 |  |
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| Playoffs | 12.05.21 | Raith Rovers | - | Dundee FC | 0:3 | ||||
| Playoffs | 15.05.21 | Dundee FC | - | Raith Rovers | 0:1 | ||||
| Championship | 08.10.22 | Arbroath FC | - | Dundee FC | 1:1 |  |
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| Championship | 08.04.23 | Arbroath FC | - | Dundee FC | 0:0 |
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