| 1 | 14/7/2018 | 1-0 v FalkirkFalkirk 0-1 Montrose | Betfred Cup Group B |
| 2 | 21/7/2018 | 0-1 v St JohnstoneMontrose 0-1 St Johnstone | Betfred Cup Group B |
| 3 | 4/8/2018 | 0-4 v ArbroathMontrose 0-4 Arbroath | Ladbrokes League One |
| 4 | 15/8/2018 | 2-2 v Cove RangersCove Rangers 2-2 Montrose | IRN-BRU Cup First Round |
| 5 | 25/8/2018 | 0-2 v StranraerStranraer 2-0 Montrose | Ladbrokes League One |
| 6 | 8/9/2018 | 1-0 v DumbartonDumbarton 0-1 Montrose | IRN-BRU Cup Second Round |
| 7 | 15/9/2018 | 1-2 v DumbartonDumbarton 2-1 Montrose | Ladbrokes League One |
| 8 | 22/9/2018 | 1-1 v Raith RoversRaith Rovers 1-1 Montrose | Ladbrokes League One |
| 9 | 29/9/2018 | 2-2 v Forfar AthleticMontrose 2-2 Forfar Athletic | Ladbrokes League One |
| 10 | 6/10/2018 | 2-3 v StenhousemuirStenhousemuir 3-2 Montrose | Ladbrokes League One |
| 11 | 13/10/2018 | 1-3 v Ross CountyRoss County 3-1 Montrose | IRN-BRU Cup Third Round |
| 12 | 20/10/2018 | 0-3 v AirdrieoniansMontrose 0-3 Airdrieonians | Ladbrokes League One |
| 13 | 27/10/2018 | 3-1 v Brechin CityBrechin City 1-3 Montrose | Ladbrokes League One |
| 14 | 3/11/2018 | 1-0 v DumbartonMontrose 1-0 Dumbarton | Ladbrokes League One |
| 15 | 17/11/2018 | 1-1 v StranraerMontrose 1-1 Stranraer | Ladbrokes League One |
| 16 | 24/11/2018 | 0-0 v Annan AthleticMontrose 0-0 Annan Athletic | William Hill Scottish Cup Third Round |
| 17 | 1/12/2018 | 2-0 v East FifeEast Fife 0-2 Montrose | Ladbrokes League One |
| 18 | 8/12/2018 | 3-2 v Raith RoversMontrose 3-2 Raith Rovers | Ladbrokes League One |
| 19 | 15/12/2018 | 1-2 v Forfar AthleticForfar Athletic 2-1 Montrose | Ladbrokes League One |
| 20 | 22/12/2018 | 3-1 v StenhousemuirMontrose 3-1 Stenhousemuir | Ladbrokes League One |
| 21 | 29/12/2018 | 1-1 v ArbroathMontrose 1-1 Arbroath | Ladbrokes League One |
| 22 | 5/1/2019 | 2-1 v StranraerStranraer 1-2 Montrose | Ladbrokes League One |
| 23 | 12/1/2019 | 0-2 v East FifeMontrose 0-2 East Fife | Ladbrokes League One |
| 24 | 19/1/2019 | 0-4 v Dundee UnitedMontrose 0-4 Dundee United | William Hill Scottish Cup Fourth Round |
| 25 | 26/1/2019 | 1-1 v DumbartonDumbarton 1-1 Montrose | Ladbrokes League One |
| 26 | 2/2/2019 | 5-2 v Brechin CityMontrose 5-2 Brechin City | Ladbrokes League One |
| 27 | 16/2/2019 | 2-0 v Forfar AthleticMontrose 2-0 Forfar Athletic | Ladbrokes League One |
