| 1 | Tue 17 Jul 2018 | 4-0 v Albion RoversStenhousemuir 4-0 Albion Rovers | Betfred Cup Group E |
| 2 | Sat 21 Jul 2018 | 0-2 v Greenock MortonGreenock Morton 2-0 Stenhousemuir | Betfred Cup Group E |
| 3 | Tue 24 Jul 2018 | 0-5 v Ayr UnitedAyr United 5-0 Stenhousemuir | Betfred Cup Group E |
| 4 | Tue 14 Aug 2018 | 0-3 v Queen of the SouthStenhousemuir 0-3 Queen of the South | IRN-BRU Cup First Round |
| 5 | Sat 25 Aug 2018 | 0-2 v Forfar AthleticForfar Athletic 2-0 Stenhousemuir | Ladbrokes League One |
| 6 | Sat 1 Sep 2018 | 2-1 v DumbartonStenhousemuir 2-1 Dumbarton | Ladbrokes League One |
| 7 | Sat 15 Sep 2018 | 0-2 v StranraerStranraer 2-0 Stenhousemuir | Ladbrokes League One |
| 8 | Sat 6 Oct 2018 | 3-2 v MontroseStenhousemuir 3-2 Montrose | Ladbrokes League One |
| 9 | Sat 10 Nov 2018 | 1-2 v DumbartonDumbarton 2-1 Stenhousemuir | Ladbrokes League One |
| 10 | Sat 17 Nov 2018 | 1-3 v Raith RoversStenhousemuir 1-3 Raith Rovers | Ladbrokes League One |
| 11 | Sat 22 Dec 2018 | 1-3 v MontroseMontrose 3-1 Stenhousemuir | Ladbrokes League One |
| 12 | Sat 29 Dec 2018 | 2-2 v DumbartonStenhousemuir 2-2 Dumbarton | Ladbrokes League One |
| 13 | Sat 5 Jan 2019 | 1-5 v Raith RoversRaith Rovers 5-1 Stenhousemuir | Ladbrokes League One |
| 14 | Sat 12 Jan 2019 | 1-4 v ArbroathStenhousemuir 1-4 Arbroath | Ladbrokes League One |
| 15 | Sat 26 Jan 2019 | 1-0 v AirdrieoniansStenhousemuir 1-0 Airdrieonians | Ladbrokes League One |
| 16 | Tue 29 Jan 2019 | 1-4 v AberdeenStenhousemuir 1-4 Aberdeen | William Hill Scottish Cup Fourth Round Replay |
| 17 | Sat 9 Feb 2019 | 1-0 v MontroseStenhousemuir 1-0 Montrose | Ladbrokes League One |
| 18 | Sat 23 Feb 2019 | 1-2 v Forfar AthleticForfar Athletic 2-1 Stenhousemuir | Ladbrokes League One |
| 19 | Tue 26 Feb 2019 | 1-1 v StranraerStranraer 1-1 Stenhousemuir | Ladbrokes League One |
| 20 | Sat 2 Mar 2019 | 1-1 v Brechin CityStenhousemuir 1-1 Brechin City | Ladbrokes League One |
| 21 | Sat 9 Mar 2019 | 2-0 v ArbroathArbroath 0-2 Stenhousemuir | Ladbrokes League One |
| 22 | Tue 12 Mar 2019 | 1-1 v East FifeEast Fife 1-1 Stenhousemuir | Ladbrokes League One |
| 23 | Sat 16 Mar 2019 | 0-1 v StranraerStenhousemuir 0-1 Stranraer | Ladbrokes League One |
| 24 | Sat 23 Mar 2019 | 0-2 v MontroseMontrose 2-0 Stenhousemuir | Ladbrokes League One |
| 25 | Sat 30 Mar 2019 | 2-1 v DumbartonDumbarton 1-2 Stenhousemuir | Ladbrokes League One |
| 26 | Sat 6 Apr 2019 | 1-1 v Raith RoversStenhousemuir 1-1 Raith Rovers | Ladbrokes League One |
| 27 | Sat 13 Apr 2019 | 1-0 v AirdrieoniansAirdrieonians 0-1 Stenhousemuir | Ladbrokes League One |
| 28 | Sat 20 Apr 2019 | 0-3 v Forfar AthleticStenhousemuir 0-3 Forfar Athletic | Ladbrokes League One |
| 29 | Sat 27 Apr 2019 | 1-1 v East FifeStenhousemuir 1-1 East Fife | Ladbrokes League One |
| 30 | Sat 4 May 2019 | 1-1 v Brechin CityBrechin City 1-1 Stenhousemuir | Ladbrokes League One |
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