| 1 | 4/8/2018 | 0-4 v ArbroathMontrose 0-4 Arbroath | Ladbrokes League One |
| 2 | 15/8/2018 | 2-2 v Cove RangersCove Rangers 2-2 Montrose | IRN-BRU Cup First Round |
| 3 | 25/8/2018 | 0-2 v StranraerStranraer 2-0 Montrose | Ladbrokes League One |
| 4 | 8/9/2018 | 1-0 v DumbartonDumbarton 0-1 Montrose | IRN-BRU Cup Second Round |
| 5 | 15/9/2018 | 1-2 v DumbartonDumbarton 2-1 Montrose | Ladbrokes League One |
| 6 | 22/9/2018 | 1-1 v Raith RoversRaith Rovers 1-1 Montrose | Ladbrokes League One |
| 7 | 6/10/2018 | 2-3 v StenhousemuirStenhousemuir 3-2 Montrose | Ladbrokes League One |
| 8 | 13/10/2018 | 1-3 v Ross CountyRoss County 3-1 Montrose | IRN-BRU Cup Third Round |
| 9 | 10/11/2018 | 0-2 v ArbroathArbroath 2-0 Montrose | Ladbrokes League One |
| 10 | 24/11/2018 | 0-0 v Annan AthleticMontrose 0-0 Annan Athletic | William Hill Scottish Cup Third Round |
| 11 | 8/12/2018 | 3-2 v Raith RoversMontrose 3-2 Raith Rovers | Ladbrokes League One |
| 12 | 22/12/2018 | 3-1 v StenhousemuirMontrose 3-1 Stenhousemuir | Ladbrokes League One |
| 13 | 5/1/2019 | 2-1 v StranraerStranraer 1-2 Montrose | Ladbrokes League One |
| 14 | 12/1/2019 | 0-2 v East FifeMontrose 0-2 East Fife | Ladbrokes League One |
| 15 | 26/1/2019 | 1-1 v DumbartonDumbarton 1-1 Montrose | Ladbrokes League One |
| 16 | 2/3/2019 | 0-1 v AirdrieoniansAirdrieonians 1-0 Montrose | Ladbrokes League One |
| 17 | 9/3/2019 | 1-3 v DumbartonMontrose 1-3 Dumbarton | Ladbrokes League One |
| 18 | 30/3/2019 | 3-1 v StranraerMontrose 3-1 Stranraer | Ladbrokes League One |
| 19 | 27/4/2019 | 0-1 v Forfar AthleticForfar Athletic 1-0 Montrose | Ladbrokes League One |
| 20 | 4/5/2019 | 1-1 v Raith RoversMontrose 1-1 Raith Rovers | Ladbrokes League One |
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