| 1 | Sat 19 Jan 2019 | 1-1 v AberdeenAberdeen 1-1 Stenhousemuir | William Hill Scottish Cup Fourth Round |
| 2 | Sat 26 Jan 2019 | 1-0 v AirdrieoniansStenhousemuir 1-0 Airdrieonians | Ladbrokes League One |
| 3 | Tue 29 Jan 2019 | 1-4 v AberdeenStenhousemuir 1-4 Aberdeen | William Hill Scottish Cup Fourth Round Replay |
| 4 | Sat 9 Feb 2019 | 1-0 v MontroseStenhousemuir 1-0 Montrose | Ladbrokes League One |
| 5 | Sat 23 Feb 2019 | 1-2 v Forfar AthleticForfar Athletic 2-1 Stenhousemuir | Ladbrokes League One |
| 6 | Tue 26 Feb 2019 | 1-1 v StranraerStranraer 1-1 Stenhousemuir | Ladbrokes League One |
| 7 | Sat 2 Mar 2019 | 1-1 v Brechin CityStenhousemuir 1-1 Brechin City | Ladbrokes League One |
| 8 | Sat 9 Mar 2019 | 2-0 v ArbroathArbroath 0-2 Stenhousemuir | Ladbrokes League One |
| 9 | Tue 12 Mar 2019 | 1-1 v East FifeEast Fife 1-1 Stenhousemuir | Ladbrokes League One |
| 10 | Sat 16 Mar 2019 | 0-1 v StranraerStenhousemuir 0-1 Stranraer | Ladbrokes League One |
| 11 | Sat 23 Mar 2019 | 0-2 v MontroseMontrose 2-0 Stenhousemuir | Ladbrokes League One |
| 12 | Sat 30 Mar 2019 | 2-1 v DumbartonDumbarton 1-2 Stenhousemuir | Ladbrokes League One |
| 13 | Sat 6 Apr 2019 | 1-1 v Raith RoversStenhousemuir 1-1 Raith Rovers | Ladbrokes League One |
| 14 | Sat 13 Apr 2019 | 1-0 v AirdrieoniansAirdrieonians 0-1 Stenhousemuir | Ladbrokes League One |
| 15 | Sat 20 Apr 2019 | 0-3 v Forfar AthleticStenhousemuir 0-3 Forfar Athletic | Ladbrokes League One |
| 16 | Sat 4 May 2019 | 1-1 v Brechin CityBrechin City 1-1 Stenhousemuir | Ladbrokes League One |
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