| 1 | Sat 22 Dec 2018 | 0-2 v Edinburgh CityCowdenbeath 0-2 Edinburgh City |
| 2 | Sat 29 Dec 2018 | 1-2 v Stirling AlbionStirling Albion 2-1 Cowdenbeath |
| 3 | Sat 5 Jan 2019 | 2-0 v Berwick RangersCowdenbeath 2-0 Berwick Rangers |
| 4 | Sat 12 Jan 2019 | 4-1 v Elgin CityElgin City 1-4 Cowdenbeath |
| 5 | Sat 26 Jan 2019 | 0-1 v ClydeClyde 1-0 Cowdenbeath |
| 6 | Sat 9 Feb 2019 | 1-1 v Queens ParkQueens Park 1-1 Cowdenbeath |
| 7 | Sat 16 Feb 2019 | 2-4 v Annan AthleticCowdenbeath 2-4 Annan Athletic |
| 8 | Tue 19 Feb 2019 | 1-0 v Albion RoversCowdenbeath 1-0 Albion Rovers |
| 9 | Sat 23 Feb 2019 | 0-2 v Edinburgh CityEdinburgh City 2-0 Cowdenbeath |
| 10 | Tue 26 Feb 2019 | 0-1 v PeterheadPeterhead 1-0 Cowdenbeath |
| 11 | Sat 2 Mar 2019 | 1-2 v Stirling AlbionCowdenbeath 1-2 Stirling Albion |
| 12 | Tue 5 Mar 2019 | 1-3 v PeterheadCowdenbeath 1-3 Peterhead |
| 13 | Sat 9 Mar 2019 | 1-1 v Berwick RangersBerwick Rangers 1-1 Cowdenbeath |
| 14 | Sat 23 Mar 2019 | 0-0 v Queens ParkCowdenbeath 0-0 Queens Park |
| 15 | Tue 26 Mar 2019 | 0-1 v Albion RoversAlbion Rovers 1-0 Cowdenbeath |
| 16 | Sat 30 Mar 2019 | 1-2 v PeterheadPeterhead 2-1 Cowdenbeath |
| 17 | Sat 6 Apr 2019 | 4-1 v Edinburgh CityCowdenbeath 4-1 Edinburgh City |
| 18 | Sat 13 Apr 2019 | 2-1 v Elgin CityCowdenbeath 2-1 Elgin City |
| 19 | Sat 20 Apr 2019 | 1-0 v Stirling AlbionStirling Albion 0-1 Cowdenbeath |
| 20 | Sat 27 Apr 2019 | 2-3 v Annan AthleticAnnan Athletic 3-2 Cowdenbeath |
| 21 | Sat 4 May 2019 | 2-1 v ClydeCowdenbeath 2-1 Clyde |
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