| 1 | 25/7/2018 | 1-3 v Forfar AthleticForfar Athletic 3-1 Montrose | Betfred Cup Group B |
| 2 | 4/8/2018 | 0-4 v ArbroathMontrose 0-4 Arbroath | Ladbrokes League One |
| 3 | 11/8/2018 | 1-0 v AirdrieoniansAirdrieonians 0-1 Montrose | Ladbrokes League One |
| 4 | 8/9/2018 | 1-0 v DumbartonDumbarton 0-1 Montrose | IRN-BRU Cup Second Round |
| 5 | 22/9/2018 | 1-1 v Raith RoversRaith Rovers 1-1 Montrose | Ladbrokes League One |
| 6 | 29/9/2018 | 2-2 v Forfar AthleticMontrose 2-2 Forfar Athletic | 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 | 20/10/2018 | 0-3 v AirdrieoniansMontrose 0-3 Airdrieonians | Ladbrokes League One |
| 10 | 27/10/2018 | 3-1 v Brechin CityBrechin City 1-3 Montrose | Ladbrokes League One |
| 11 | 3/11/2018 | 1-0 v DumbartonMontrose 1-0 Dumbarton | Ladbrokes League One |
| 12 | 10/11/2018 | 0-2 v ArbroathArbroath 2-0 Montrose | Ladbrokes League One |
| 13 | 1/12/2018 | 2-0 v East FifeEast Fife 0-2 Montrose | Ladbrokes League One |
| 14 | 22/12/2018 | 3-1 v StenhousemuirMontrose 3-1 Stenhousemuir | Ladbrokes League One |
| 15 | 5/1/2019 | 2-1 v StranraerStranraer 1-2 Montrose | Ladbrokes League One |
| 16 | 19/1/2019 | 0-4 v Dundee UnitedMontrose 0-4 Dundee United | William Hill Scottish Cup Fourth Round |
| 17 | 26/1/2019 | 1-1 v DumbartonDumbarton 1-1 Montrose | Ladbrokes League One |
| 18 | 2/2/2019 | 5-2 v Brechin CityMontrose 5-2 Brechin City | Ladbrokes League One |
| 19 | 9/2/2019 | 0-1 v StenhousemuirStenhousemuir 1-0 Montrose | Ladbrokes League One |
| 20 | 16/2/2019 | 2-0 v Forfar AthleticMontrose 2-0 Forfar Athletic | Ladbrokes League One |
| 21 | 23/2/2019 | 1-4 v Raith RoversRaith Rovers 4-1 Montrose | Ladbrokes League One |
| 22 | 2/3/2019 | 0-1 v AirdrieoniansAirdrieonians 1-0 Montrose | Ladbrokes League One |
| 23 | 30/3/2019 | 3-1 v StranraerMontrose 3-1 Stranraer | Ladbrokes League One |
| 24 | 6/4/2019 | 0-1 v ArbroathArbroath 1-0 Montrose | Ladbrokes League One |
| 25 | 13/4/2019 | 2-0 v East FifeEast Fife 0-2 Montrose | Ladbrokes League One |
| 26 | 20/4/2019 | 2-1 v AirdrieoniansMontrose 2-1 Airdrieonians | Ladbrokes League One |
| 27 | 27/4/2019 | 0-1 v Forfar AthleticForfar Athletic 1-0 Montrose | Ladbrokes League One |
| 28 | 4/5/2019 | 1-1 v Raith RoversMontrose 1-1 Raith Rovers | Ladbrokes League One |
