| 1 | 24/7/2018 | 0-5 v Ayr UnitedAyr United 5-0 Stenhousemuir | Betfred Cup Group E |
| 2 | 14/8/2018 | 0-3 v Queen of the SouthStenhousemuir 0-3 Queen of the South | IRN-BRU Cup First Round |
| 3 | 25/8/2018 | 0-2 v Forfar AthleticForfar Athletic 2-0 Stenhousemuir | Ladbrokes League One |
| 4 | 1/9/2018 | 2-1 v DumbartonStenhousemuir 2-1 Dumbarton | Ladbrokes League One |
| 5 | 29/9/2018 | 0-2 v East FifeEast Fife 2-0 Stenhousemuir | Ladbrokes League One |
| 6 | 6/10/2018 | 3-2 v MontroseStenhousemuir 3-2 Montrose | Ladbrokes League One |
| 7 | 20/10/2018 | 1-2 v Forfar AthleticStenhousemuir 1-2 Forfar Athletic | Ladbrokes League One |
| 8 | 27/10/2018 | 1-0 v AirdrieoniansAirdrieonians 0-1 Stenhousemuir | Ladbrokes League One |
| 9 | 3/11/2018 | 0-2 v StranraerStenhousemuir 0-2 Stranraer | Ladbrokes League One |
| 10 | 17/11/2018 | 1-3 v Raith RoversStenhousemuir 1-3 Raith Rovers | Ladbrokes League One |
| 11 | 15/12/2018 | 0-2 v East FifeStenhousemuir 0-2 East Fife | Ladbrokes League One |
| 12 | 22/12/2018 | 1-3 v MontroseMontrose 3-1 Stenhousemuir | Ladbrokes League One |
| 13 | 12/1/2019 | 1-4 v ArbroathStenhousemuir 1-4 Arbroath | Ladbrokes League One |
