| 1 | Sat 4 Aug 2018 | 0-4 v ArbroathMontrose 0-4 Arbroath |
| 2 | Sat 25 Aug 2018 | 0-2 v StranraerStranraer 2-0 Montrose |
| 3 | Sat 15 Sep 2018 | 1-2 v DumbartonDumbarton 2-1 Montrose |
| 4 | Sat 22 Sep 2018 | 1-1 v Raith RoversRaith Rovers 1-1 Montrose |
| 5 | Sat 29 Sep 2018 | 2-2 v Forfar AthleticMontrose 2-2 Forfar Athletic |
| 6 | Sat 6 Oct 2018 | 2-3 v StenhousemuirStenhousemuir 3-2 Montrose |
| 7 | Sat 20 Oct 2018 | 0-3 v AirdrieoniansMontrose 0-3 Airdrieonians |
| 8 | Sat 27 Oct 2018 | 3-1 v Brechin CityBrechin City 1-3 Montrose |
| 9 | Sat 3 Nov 2018 | 1-0 v DumbartonMontrose 1-0 Dumbarton |
| 10 | Sat 17 Nov 2018 | 1-1 v StranraerMontrose 1-1 Stranraer |
| 11 | Sat 1 Dec 2018 | 2-0 v East FifeEast Fife 0-2 Montrose |
| 12 | Sat 8 Dec 2018 | 3-2 v Raith RoversMontrose 3-2 Raith Rovers |
| 13 | Sat 15 Dec 2018 | 1-2 v Forfar AthleticForfar Athletic 2-1 Montrose |
| 14 | Sat 22 Dec 2018 | 3-1 v StenhousemuirMontrose 3-1 Stenhousemuir |
| 15 | Sat 29 Dec 2018 | 1-1 v ArbroathMontrose 1-1 Arbroath |
| 16 | Sat 5 Jan 2019 | 2-1 v StranraerStranraer 1-2 Montrose |
| 17 | Sat 12 Jan 2019 | 0-2 v East FifeMontrose 0-2 East Fife |
| 18 | Sat 26 Jan 2019 | 1-1 v DumbartonDumbarton 1-1 Montrose |
| 19 | Sat 2 Feb 2019 | 5-2 v Brechin CityMontrose 5-2 Brechin City |
| 20 | Sat 16 Feb 2019 | 2-0 v Forfar AthleticMontrose 2-0 Forfar Athletic |
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