| 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 | Sat 25 Aug 2018 | 0-2 v Forfar AthleticForfar Athletic 2-0 Stenhousemuir | Ladbrokes League One |
| 4 | Sat 1 Sep 2018 | 2-1 v DumbartonStenhousemuir 2-1 Dumbarton | Ladbrokes League One |
| 5 | Sat 15 Sep 2018 | 0-2 v StranraerStranraer 2-0 Stenhousemuir | Ladbrokes League One |
| 6 | Sat 22 Sep 2018 | 1-2 v ArbroathStenhousemuir 1-2 Arbroath | Ladbrokes League One |
| 7 | Sat 29 Sep 2018 | 0-2 v East FifeEast Fife 2-0 Stenhousemuir | Ladbrokes League One |
| 8 | Sat 20 Oct 2018 | 1-2 v Forfar AthleticStenhousemuir 1-2 Forfar Athletic | Ladbrokes League One |
| 9 | Sat 3 Nov 2018 | 0-2 v StranraerStenhousemuir 0-2 Stranraer | Ladbrokes League One |
| 10 | Sat 10 Nov 2018 | 1-2 v DumbartonDumbarton 2-1 Stenhousemuir | Ladbrokes League One |
| 11 | Sat 1 Dec 2018 | 2-5 v ArbroathArbroath 5-2 Stenhousemuir | Ladbrokes League One |
| 12 | Sat 8 Dec 2018 | 2-1 v Brechin CityBrechin City 1-2 Stenhousemuir | Ladbrokes League One |
| 13 | Sat 22 Dec 2018 | 1-3 v MontroseMontrose 3-1 Stenhousemuir | Ladbrokes League One |
| 14 | Sat 29 Dec 2018 | 2-2 v DumbartonStenhousemuir 2-2 Dumbarton | Ladbrokes League One |
| 15 | Sat 5 Jan 2019 | 1-5 v Raith RoversRaith Rovers 5-1 Stenhousemuir | Ladbrokes League One |
| 16 | Sat 12 Jan 2019 | 1-4 v ArbroathStenhousemuir 1-4 Arbroath | Ladbrokes League One |
| 17 | Sat 26 Jan 2019 | 1-0 v AirdrieoniansStenhousemuir 1-0 Airdrieonians | Ladbrokes League One |
| 18 | Sat 30 Mar 2019 | 2-1 v DumbartonDumbarton 1-2 Stenhousemuir | Ladbrokes League One |
| 19 | Sat 20 Apr 2019 | 0-3 v Forfar AthleticStenhousemuir 0-3 Forfar Athletic | Ladbrokes League One |
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