| 1 | Sat 14 Jul 2018 | 2-0 v Raith RoversRaith Rovers 0-2 Cowdenbeath | Betfred Cup Group C |
| 2 | Tue 17 Jul 2018 | 2-5 v Inverness Caledonian ThistleCowdenbeath 2-5 Inverness Caledonian Thistle | Betfred Cup Group C |
| 3 | Sat 21 Jul 2018 | 1-0 v Cove RangersCowdenbeath 1-0 Cove Rangers | Betfred Cup Group C |
| 4 | Tue 24 Jul 2018 | 0-5 v Heart of MidlothianHeart of Midlothian 5-0 Cowdenbeath | Betfred Cup Group C |
| 5 | Tue 14 Aug 2018 | 1-3 v East FifeCowdenbeath 1-3 East Fife | IRN-BRU Cup First Round |
| 6 | Sat 20 Oct 2018 | 2-1 v ClydeCowdenbeath 2-1 Clyde | William Hill Scottish Cup Second Round |
| 7 | Sat 24 Nov 2018 | 1-0 v Brora RangersCowdenbeath 1-0 Brora Rangers | William Hill Scottish Cup Third Round |
| 8 | Sat 22 Dec 2018 | 0-2 v Edinburgh CityCowdenbeath 0-2 Edinburgh City | Ladbrokes League Two |
| 9 | Sat 29 Dec 2018 | 1-2 v Stirling AlbionStirling Albion 2-1 Cowdenbeath | Ladbrokes League Two |
| 10 | Sat 5 Jan 2019 | 2-0 v Berwick RangersCowdenbeath 2-0 Berwick Rangers | Ladbrokes League Two |
| 11 | Sat 9 Feb 2019 | 1-0 v MontroseStenhousemuir 1-0 Montrose | Ladbrokes League One |
| 12 | Sat 23 Feb 2019 | 1-2 v Forfar AthleticForfar Athletic 2-1 Stenhousemuir | Ladbrokes League One |
| 13 | Tue 26 Feb 2019 | 1-1 v StranraerStranraer 1-1 Stenhousemuir | Ladbrokes League One |
| 14 | Sat 2 Mar 2019 | 1-1 v Brechin CityStenhousemuir 1-1 Brechin City | Ladbrokes League One |
| 15 | Sat 9 Mar 2019 | 2-0 v ArbroathArbroath 0-2 Stenhousemuir | Ladbrokes League One |
| 16 | Tue 12 Mar 2019 | 1-1 v East FifeEast Fife 1-1 Stenhousemuir | Ladbrokes League One |
| 17 | Sat 16 Mar 2019 | 0-1 v StranraerStenhousemuir 0-1 Stranraer | Ladbrokes League One |
| 18 | Sat 23 Mar 2019 | 0-2 v MontroseMontrose 2-0 Stenhousemuir | Ladbrokes League One |
| 19 | Sat 30 Mar 2019 | 2-1 v DumbartonDumbarton 1-2 Stenhousemuir | Ladbrokes League One |
| 20 | Sat 6 Apr 2019 | 1-1 v Raith RoversStenhousemuir 1-1 Raith Rovers | Ladbrokes League One |
| 21 | Sat 13 Apr 2019 | 1-0 v AirdrieoniansAirdrieonians 0-1 Stenhousemuir | Ladbrokes League One |
| 22 | Sat 20 Apr 2019 | 0-3 v Forfar AthleticStenhousemuir 0-3 Forfar Athletic | Ladbrokes League One |
| 23 | Sat 27 Apr 2019 | 1-1 v East FifeStenhousemuir 1-1 East Fife | Ladbrokes League One |
| 24 | Sat 4 May 2019 | 1-1 v Brechin CityBrechin City 1-1 Stenhousemuir | Ladbrokes League One |
Football Web Pages