| 1 | Sat 20 Oct 2018 | 2-1 v ClydeCowdenbeath 2-1 Clyde | William Hill Scottish Cup Second Round |
| 2 | Sat 24 Nov 2018 | 1-0 v Brora RangersCowdenbeath 1-0 Brora Rangers | William Hill Scottish Cup Third Round |
| 3 | Sat 22 Dec 2018 | 0-2 v Edinburgh CityCowdenbeath 0-2 Edinburgh City | Ladbrokes League Two |
| 4 | Sat 29 Dec 2018 | 1-2 v Stirling AlbionStirling Albion 2-1 Cowdenbeath | Ladbrokes League Two |
| 5 | Sat 12 Jan 2019 | 4-1 v Elgin CityElgin City 1-4 Cowdenbeath | Ladbrokes League Two |
| 6 | Sat 26 Jan 2019 | 0-1 v ClydeClyde 1-0 Cowdenbeath | Ladbrokes League Two |
| 7 | Sat 9 Feb 2019 | 1-1 v Queens ParkQueens Park 1-1 Cowdenbeath | Ladbrokes League Two |
| 8 | Tue 19 Feb 2019 | 1-0 v Albion RoversCowdenbeath 1-0 Albion Rovers | Ladbrokes League Two |
| 9 | Sat 23 Feb 2019 | 0-2 v Edinburgh CityEdinburgh City 2-0 Cowdenbeath | Ladbrokes League Two |
| 10 | Tue 26 Feb 2019 | 0-1 v PeterheadPeterhead 1-0 Cowdenbeath | Ladbrokes League Two |
| 11 | Sat 2 Mar 2019 | 1-2 v Stirling AlbionCowdenbeath 1-2 Stirling Albion | Ladbrokes League Two |
| 12 | Tue 5 Mar 2019 | 1-3 v PeterheadCowdenbeath 1-3 Peterhead | Ladbrokes League Two |
| 13 | Sat 9 Mar 2019 | 1-1 v Berwick RangersBerwick Rangers 1-1 Cowdenbeath | Ladbrokes League Two |
| 14 | Sat 30 Mar 2019 | 1-2 v PeterheadPeterhead 2-1 Cowdenbeath | Ladbrokes League Two |
| 15 | Sat 6 Apr 2019 | 4-1 v Edinburgh CityCowdenbeath 4-1 Edinburgh City | Ladbrokes League Two |
| 16 | Sat 13 Apr 2019 | 2-1 v Elgin CityCowdenbeath 2-1 Elgin City | Ladbrokes League Two |
| 17 | Sat 20 Apr 2019 | 1-0 v Stirling AlbionStirling Albion 0-1 Cowdenbeath | Ladbrokes League Two |
| 18 | Sat 27 Apr 2019 | 2-3 v Annan AthleticAnnan Athletic 3-2 Cowdenbeath | Ladbrokes League Two |
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