| 1 | Sat 4 Aug 2018 | 0-4 v ArbroathMontrose 0-4 Arbroath | Ladbrokes League One |
| 2 | Wed 15 Aug 2018 | 2-2 v Cove RangersCove Rangers 2-2 Montrose | IRN-BRU Cup First Round |
| 3 | Sat 25 Aug 2018 | 0-2 v StranraerStranraer 2-0 Montrose | Ladbrokes League One |
| 4 | Sat 8 Sep 2018 | 1-0 v DumbartonDumbarton 0-1 Montrose | IRN-BRU Cup Second Round |
| 5 | Sat 15 Sep 2018 | 1-2 v DumbartonDumbarton 2-1 Montrose | Ladbrokes League One |
| 6 | Sat 22 Sep 2018 | 1-1 v Raith RoversRaith Rovers 1-1 Montrose | Ladbrokes League One |
| 7 | Sat 6 Oct 2018 | 2-3 v StenhousemuirStenhousemuir 3-2 Montrose | Ladbrokes League One |
| 8 | Sat 13 Oct 2018 | 1-3 v Ross CountyRoss County 3-1 Montrose | IRN-BRU Cup Third Round |
| 9 | Sat 10 Nov 2018 | 0-2 v ArbroathArbroath 2-0 Montrose | Ladbrokes League One |
| 10 | Sat 24 Nov 2018 | 0-0 v Annan AthleticMontrose 0-0 Annan Athletic | William Hill Scottish Cup Third Round |
| 11 | Sat 8 Dec 2018 | 3-2 v Raith RoversMontrose 3-2 Raith Rovers | Ladbrokes League One |
| 12 | Sat 22 Dec 2018 | 3-1 v StenhousemuirMontrose 3-1 Stenhousemuir | Ladbrokes League One |
| 13 | Sat 5 Jan 2019 | 2-1 v StranraerStranraer 1-2 Montrose | Ladbrokes League One |
| 14 | Sat 12 Jan 2019 | 0-2 v East FifeMontrose 0-2 East Fife | Ladbrokes League One |
| 15 | Sat 26 Jan 2019 | 1-1 v DumbartonDumbarton 1-1 Montrose | Ladbrokes League One |
| 16 | Sat 2 Mar 2019 | 0-1 v AirdrieoniansAirdrieonians 1-0 Montrose | Ladbrokes League One |
| 17 | Sat 9 Mar 2019 | 1-3 v DumbartonMontrose 1-3 Dumbarton | Ladbrokes League One |
| 18 | Sat 30 Mar 2019 | 3-1 v StranraerMontrose 3-1 Stranraer | Ladbrokes League One |
| 19 | Sat 27 Apr 2019 | 0-1 v Forfar AthleticForfar Athletic 1-0 Montrose | Ladbrokes League One |
| 20 | Sat 4 May 2019 | 1-1 v Raith RoversMontrose 1-1 Raith Rovers | Ladbrokes League One |
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