| 1 | Tue 13 Aug 2019 | 2-1 v Forfar AthleticMontrose 2-1 Forfar Athletic | Tunnock's Challenge Cup Second Round |
| 2 | Sat 17 Aug 2019 | 1-2 v FalkirkFalkirk 2-1 Montrose | Ladbrokes League One |
| 3 | Sat 24 Aug 2019 | 0-3 v Raith RoversRaith Rovers 3-0 Montrose | Ladbrokes League One |
| 4 | Sat 31 Aug 2019 | 1-2 v DumbartonMontrose 1-2 Dumbarton | Ladbrokes League One |
| 5 | Sat 28 Sep 2019 | 1-2 v Raith RoversForfar Athletic 1-2 Raith Rovers | Ladbrokes League One |
| 6 | Sat 5 Oct 2019 | 1-3 v DumbartonDumbarton 3-1 Forfar Athletic | Ladbrokes League One |
| 7 | Sat 19 Oct 2019 | 0-1 v East FifeEast Fife 1-0 Forfar Athletic | Ladbrokes League One |
| 8 | Sat 26 Oct 2019 | 1-4 v AirdrieoniansForfar Athletic 1-4 Airdrieonians | Ladbrokes League One |
| 9 | Sat 4 Jan 2020 | 0-1 v AirdrieoniansAirdrieonians 1-0 Forfar Athletic | Ladbrokes League One |
| 10 | Sat 29 Feb 2020 | 1-0 v AirdrieoniansMontrose 1-0 Airdrieonians | Ladbrokes League One |
| 11 | Sat 7 Mar 2020 | 4-1 v StranraerMontrose 4-1 Stranraer | Ladbrokes League One |
| 12 | Tue 10 Mar 2020 | 1-0 v StranraerStranraer 0-1 Montrose | Ladbrokes League One |
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