| 1 | Sat 4 Aug 2018 | 1-1 v StranraerStranraer 1-1 Raith Rovers |
| 2 | Sat 11 Aug 2018 | 2-0 v StenhousemuirRaith Rovers 2-0 Stenhousemuir |
| 3 | Sat 15 Sep 2018 | 1-1 v Brechin CityBrechin City 1-1 Raith Rovers |
| 4 | Sat 22 Sep 2018 | 1-1 v MontroseRaith Rovers 1-1 Montrose |
| 5 | Sat 6 Oct 2018 | 1-1 v ArbroathRaith Rovers 1-1 Arbroath |
| 6 | Sat 27 Oct 2018 | 2-3 v Forfar AthleticForfar Athletic 3-2 Raith Rovers |
| 7 | Sat 3 Nov 2018 | 2-1 v Brechin CityRaith Rovers 2-1 Brechin City |
| 8 | Sat 17 Nov 2018 | 3-1 v StenhousemuirStenhousemuir 1-3 Raith Rovers |
| 9 | Sat 1 Dec 2018 | 2-0 v AirdrieoniansRaith Rovers 2-0 Airdrieonians |
| 10 | Sat 22 Dec 2018 | 2-0 v ArbroathArbroath 0-2 Raith Rovers |
| 11 | Sat 29 Dec 2018 | 1-2 v East FifeRaith Rovers 1-2 East Fife |
| 12 | Sat 5 Jan 2019 | 5-1 v StenhousemuirRaith Rovers 5-1 Stenhousemuir |
| 13 | Sat 12 Jan 2019 | 1-1 v AirdrieoniansAirdrieonians 1-1 Raith Rovers |
| 14 | Sat 26 Jan 2019 | 1-1 v DumbartonDumbarton 1-1 Montrose |
| 15 | Sat 2 Feb 2019 | 5-2 v Brechin CityMontrose 5-2 Brechin City |
| 16 | Sat 9 Feb 2019 | 0-1 v StenhousemuirStenhousemuir 1-0 Montrose |
| 17 | Sat 16 Feb 2019 | 2-0 v Forfar AthleticMontrose 2-0 Forfar Athletic |
| 18 | Sat 2 Mar 2019 | 0-1 v AirdrieoniansAirdrieonians 1-0 Montrose |
| 19 | Sat 9 Mar 2019 | 1-3 v DumbartonMontrose 1-3 Dumbarton |
| 20 | Sat 23 Mar 2019 | 2-0 v StenhousemuirMontrose 2-0 Stenhousemuir |
| 21 | Sat 30 Mar 2019 | 3-1 v StranraerMontrose 3-1 Stranraer |
| 22 | Tue 2 Apr 2019 | 3-0 v Brechin CityBrechin City 0-3 Montrose |
| 23 | Sat 6 Apr 2019 | 0-1 v ArbroathArbroath 1-0 Montrose |
| 24 | Sat 13 Apr 2019 | 2-0 v East FifeEast Fife 0-2 Montrose |
| 25 | Sat 20 Apr 2019 | 2-1 v AirdrieoniansMontrose 2-1 Airdrieonians |
| 26 | Sat 27 Apr 2019 | 0-1 v Forfar AthleticForfar Athletic 1-0 Montrose |
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