| 1 | 17/7/2018 | 1-0 v East FifeMontrose 1-0 East Fife | Betfred Cup Group B |
| 2 | 25/7/2018 | 1-3 v Forfar AthleticForfar Athletic 3-1 Montrose | Betfred Cup Group B |
| 3 | 11/8/2018 | 1-0 v AirdrieoniansAirdrieonians 0-1 Montrose | Ladbrokes League One |
| 4 | 22/9/2018 | 1-1 v Raith RoversRaith Rovers 1-1 Montrose | Ladbrokes League One |
| 5 | 6/10/2018 | 2-3 v StenhousemuirStenhousemuir 3-2 Montrose | Ladbrokes League One |
| 6 | 13/10/2018 | 1-3 v Ross CountyRoss County 3-1 Montrose | IRN-BRU Cup Third Round |
| 7 | 20/10/2018 | 0-3 v AirdrieoniansMontrose 0-3 Airdrieonians | Ladbrokes League One |
| 8 | 27/10/2018 | 3-1 v Brechin CityBrechin City 1-3 Montrose | Ladbrokes League One |
| 9 | 17/11/2018 | 1-1 v StranraerMontrose 1-1 Stranraer | Ladbrokes League One |
| 10 | 1/12/2018 | 2-0 v East FifeEast Fife 0-2 Montrose | Ladbrokes League One |
| 11 | 8/12/2018 | 3-2 v Raith RoversMontrose 3-2 Raith Rovers | Ladbrokes League One |
| 12 | 15/12/2018 | 1-2 v Forfar AthleticForfar Athletic 2-1 Montrose | Ladbrokes League One |
| 13 | 29/12/2018 | 1-1 v ArbroathMontrose 1-1 Arbroath | Ladbrokes League One |
| 14 | 5/1/2019 | 2-1 v StranraerStranraer 1-2 Montrose | Ladbrokes League One |
| 15 | 9/3/2019 | 1-3 v DumbartonMontrose 1-3 Dumbarton | Ladbrokes League One |
| 16 | 23/3/2019 | 2-0 v StenhousemuirMontrose 2-0 Stenhousemuir | Ladbrokes League One |
| 17 | 30/3/2019 | 3-1 v StranraerMontrose 3-1 Stranraer | Ladbrokes League One |
| 18 | 2/4/2019 | 3-0 v Brechin CityBrechin City 0-3 Montrose | Ladbrokes League One |
| 19 | 6/4/2019 | 0-1 v ArbroathArbroath 1-0 Montrose | Ladbrokes League One |
| 20 | 13/4/2019 | 2-0 v East FifeEast Fife 0-2 Montrose | Ladbrokes League One |
| 21 | 20/4/2019 | 2-1 v AirdrieoniansMontrose 2-1 Airdrieonians | Ladbrokes League One |
| 22 | 27/4/2019 | 0-1 v Forfar AthleticForfar Athletic 1-0 Montrose | Ladbrokes League One |
