| 1 | Tue 17 Jul 2018 | 0-2 v FalkirkFalkirk 2-0 Forfar Athletic | Betfred Cup Group B |
| 2 | Sun 22 Jul 2018 | 1-1 v East FifeEast Fife 1-1 Forfar Athletic | Betfred Cup Group B |
| 3 | Wed 25 Jul 2018 | 3-1 v MontroseForfar Athletic 3-1 Montrose | Betfred Cup Group B |
| 4 | Sat 25 Aug 2018 | 2-0 v StenhousemuirForfar Athletic 2-0 Stenhousemuir | Ladbrokes League One |
| 5 | Sat 1 Sep 2018 | 0-4 v Raith RoversRaith Rovers 4-0 Forfar Athletic | Ladbrokes League One |
| 6 | Sat 15 Sep 2018 | 1-3 v ArbroathArbroath 3-1 Forfar Athletic | Ladbrokes League One |
| 7 | Sat 22 Sep 2018 | 1-1 v Brechin CityForfar Athletic 1-1 Brechin City | Ladbrokes League One |
| 8 | Sat 8 Dec 2018 | 2-3 v ArbroathForfar Athletic 2-3 Arbroath | Ladbrokes League One |
| 9 | Sat 15 Dec 2018 | 2-1 v MontroseForfar Athletic 2-1 Montrose | Ladbrokes League One |
| 10 | Sat 19 Jan 2019 | 1-1 v AberdeenAberdeen 1-1 Stenhousemuir | William Hill Scottish Cup Fourth Round |
| 11 | Sat 26 Jan 2019 | 1-0 v AirdrieoniansStenhousemuir 1-0 Airdrieonians | Ladbrokes League One |
| 12 | Tue 29 Jan 2019 | 1-4 v AberdeenStenhousemuir 1-4 Aberdeen | William Hill Scottish Cup Fourth Round Replay |
| 13 | Sat 9 Feb 2019 | 1-0 v MontroseStenhousemuir 1-0 Montrose | Ladbrokes League One |
| 14 | Sat 23 Feb 2019 | 1-2 v Forfar AthleticForfar Athletic 2-1 Stenhousemuir | Ladbrokes League One |
| 15 | Tue 26 Feb 2019 | 1-1 v StranraerStranraer 1-1 Stenhousemuir | Ladbrokes League One |
| 16 | Sat 2 Mar 2019 | 1-1 v Brechin CityStenhousemuir 1-1 Brechin City | Ladbrokes League One |
| 17 | Sat 9 Mar 2019 | 2-0 v ArbroathArbroath 0-2 Stenhousemuir | Ladbrokes League One |
| 18 | Tue 12 Mar 2019 | 1-1 v East FifeEast Fife 1-1 Stenhousemuir | Ladbrokes League One |
| 19 | Sat 16 Mar 2019 | 0-1 v StranraerStenhousemuir 0-1 Stranraer | Ladbrokes League One |
| 20 | Sat 23 Mar 2019 | 0-2 v MontroseMontrose 2-0 Stenhousemuir | Ladbrokes League One |
| 21 | Sat 30 Mar 2019 | 2-1 v DumbartonDumbarton 1-2 Stenhousemuir | Ladbrokes League One |
| 22 | Sat 6 Apr 2019 | 1-1 v Raith RoversStenhousemuir 1-1 Raith Rovers | Ladbrokes League One |
| 23 | Sat 13 Apr 2019 | 1-0 v AirdrieoniansAirdrieonians 0-1 Stenhousemuir | Ladbrokes League One |
| 24 | Sat 20 Apr 2019 | 0-3 v Forfar AthleticStenhousemuir 0-3 Forfar Athletic | Ladbrokes League One |
| 25 | Sat 4 May 2019 | 1-1 v Brechin CityBrechin City 1-1 Stenhousemuir | Ladbrokes League One |
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