| 1 | Tue 24 Jul 2018 | 0-5 v Ayr UnitedAyr United 5-0 Stenhousemuir | Betfred Cup Group E |
| 2 | Tue 14 Aug 2018 | 0-3 v Queen of the SouthStenhousemuir 0-3 Queen of the South | IRN-BRU Cup First Round |
| 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 29 Sep 2018 | 0-2 v East FifeEast Fife 2-0 Stenhousemuir | Ladbrokes League One |
| 6 | Sat 6 Oct 2018 | 3-2 v MontroseStenhousemuir 3-2 Montrose | Ladbrokes League One |
| 7 | Sat 20 Oct 2018 | 1-2 v Forfar AthleticStenhousemuir 1-2 Forfar Athletic | Ladbrokes League One |
| 8 | Sat 27 Oct 2018 | 1-0 v AirdrieoniansAirdrieonians 0-1 Stenhousemuir | Ladbrokes League One |
| 9 | Sat 3 Nov 2018 | 0-2 v StranraerStenhousemuir 0-2 Stranraer | Ladbrokes League One |
| 10 | Sat 17 Nov 2018 | 1-3 v Raith RoversStenhousemuir 1-3 Raith Rovers | Ladbrokes League One |
| 11 | Sat 15 Dec 2018 | 0-2 v East FifeStenhousemuir 0-2 East Fife | Ladbrokes League One |
| 12 | Sat 22 Dec 2018 | 1-3 v MontroseMontrose 3-1 Stenhousemuir | Ladbrokes League One |
| 13 | Sat 12 Jan 2019 | 1-4 v ArbroathStenhousemuir 1-4 Arbroath | Ladbrokes League One |
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