| 1 | Sat 14 Jul 2018 | 1-0 v FalkirkFalkirk 0-1 Montrose | Betfred Cup Group B |
| 2 | Tue 17 Jul 2018 | 1-0 v East FifeMontrose 1-0 East Fife | Betfred Cup Group B |
| 3 | Sat 21 Jul 2018 | 0-1 v St JohnstoneMontrose 0-1 St Johnstone | Betfred Cup Group B |
| 4 | Wed 25 Jul 2018 | 1-3 v Forfar AthleticForfar Athletic 3-1 Montrose | Betfred Cup Group B |
| 5 | Sat 4 Aug 2018 | 0-4 v ArbroathMontrose 0-4 Arbroath | Ladbrokes League One |
| 6 | Sat 11 Aug 2018 | 1-0 v AirdrieoniansAirdrieonians 0-1 Montrose | Ladbrokes League One |
| 7 | Sat 25 Aug 2018 | 0-2 v StranraerStranraer 2-0 Montrose | Ladbrokes League One |
| 8 | Sat 15 Sep 2018 | 1-2 v DumbartonDumbarton 2-1 Montrose | Ladbrokes League One |
| 9 | Sat 22 Sep 2018 | 1-1 v Raith RoversRaith Rovers 1-1 Montrose | Ladbrokes League One |
| 10 | Sat 29 Sep 2018 | 2-2 v Forfar AthleticMontrose 2-2 Forfar Athletic | Ladbrokes League One |
| 11 | Sat 6 Oct 2018 | 2-3 v StenhousemuirStenhousemuir 3-2 Montrose | Ladbrokes League One |
| 12 | Sat 13 Oct 2018 | 1-3 v Ross CountyRoss County 3-1 Montrose | IRN-BRU Cup Third Round |
| 13 | Sat 27 Oct 2018 | 3-1 v Brechin CityBrechin City 1-3 Montrose | Ladbrokes League One |
| 14 | Sat 3 Nov 2018 | 1-0 v DumbartonMontrose 1-0 Dumbarton | Ladbrokes League One |
| 15 | Sat 10 Nov 2018 | 0-2 v ArbroathArbroath 2-0 Montrose | Ladbrokes League One |
| 16 | Sat 17 Nov 2018 | 1-1 v StranraerMontrose 1-1 Stranraer | Ladbrokes League One |
| 17 | Sat 24 Nov 2018 | 0-0 v Annan AthleticMontrose 0-0 Annan Athletic | William Hill Scottish Cup Third Round |
| 18 | Tue 27 Nov 2018 | 4-3 v Annan AthleticAnnan Athletic 3-4 Montrose | William Hill Scottish Cup Third Round Replay |
| 19 | Sat 1 Dec 2018 | 2-0 v East FifeEast Fife 0-2 Montrose | Ladbrokes League One |
| 20 | Sat 8 Dec 2018 | 3-2 v Raith RoversMontrose 3-2 Raith Rovers | Ladbrokes League One |
| 21 | Sat 15 Dec 2018 | 1-2 v Forfar AthleticForfar Athletic 2-1 Montrose | Ladbrokes League One |
| 22 | Sat 22 Dec 2018 | 3-1 v StenhousemuirMontrose 3-1 Stenhousemuir | Ladbrokes League One |
| 23 | Sat 29 Dec 2018 | 1-1 v ArbroathMontrose 1-1 Arbroath | Ladbrokes League One |
| 24 | Sat 5 Jan 2019 | 2-1 v StranraerStranraer 1-2 Montrose | Ladbrokes League One |
| 25 | Sat 12 Jan 2019 | 0-2 v East FifeMontrose 0-2 East Fife | Ladbrokes League One |
| 26 | Sat 19 Jan 2019 | 0-4 v Dundee UnitedMontrose 0-4 Dundee United | William Hill Scottish Cup Fourth Round |
| 27 | Sat 26 Jan 2019 | 1-1 v DumbartonDumbarton 1-1 Montrose | Ladbrokes League One |
| 28 | Sat 2 Feb 2019 | 5-2 v Brechin CityMontrose 5-2 Brechin City | Ladbrokes League One |
| 29 | Sat 9 Feb 2019 | 0-1 v StenhousemuirStenhousemuir 1-0 Montrose | Ladbrokes League One |
| 30 | Sat 16 Feb 2019 | 2-0 v Forfar AthleticMontrose 2-0 Forfar Athletic | Ladbrokes League One |
| 31 | Sat 23 Feb 2019 | 1-4 v Raith RoversRaith Rovers 4-1 Montrose | Ladbrokes League One |
| 32 | Sat 2 Mar 2019 | 0-1 v AirdrieoniansAirdrieonians 1-0 Montrose | Ladbrokes League One |
| 33 | Sat 9 Mar 2019 | 1-3 v DumbartonMontrose 1-3 Dumbarton | Ladbrokes League One |
| 34 | Sat 23 Mar 2019 | 2-0 v StenhousemuirMontrose 2-0 Stenhousemuir | Ladbrokes League One |
| 35 | Sat 30 Mar 2019 | 3-1 v StranraerMontrose 3-1 Stranraer | Ladbrokes League One |
| 36 | Tue 2 Apr 2019 | 3-0 v Brechin CityBrechin City 0-3 Montrose | Ladbrokes League One |
| 37 | Sat 6 Apr 2019 | 0-1 v ArbroathArbroath 1-0 Montrose | Ladbrokes League One |
| 38 | Sat 20 Apr 2019 | 2-1 v AirdrieoniansMontrose 2-1 Airdrieonians | Ladbrokes League One |
| 39 | Sat 4 May 2019 | 1-1 v Raith RoversMontrose 1-1 Raith Rovers | Ladbrokes League One |
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