| 1 | 14/7/2018 | 2-0 v Raith RoversRaith Rovers 0-2 Cowdenbeath | Betfred Cup Group C |
| 2 | 17/7/2018 | 2-5 v Inverness Caledonian ThistleCowdenbeath 2-5 Inverness Caledonian Thistle | Betfred Cup Group C |
| 3 | 21/7/2018 | 1-0 v Cove RangersCowdenbeath 1-0 Cove Rangers | Betfred Cup Group C |
| 4 | 24/7/2018 | 0-5 v Heart of MidlothianHeart of Midlothian 5-0 Cowdenbeath | Betfred Cup Group C |
| 5 | 14/8/2018 | 1-3 v East FifeCowdenbeath 1-3 East Fife | IRN-BRU Cup First Round |
| 6 | 20/10/2018 | 2-1 v ClydeCowdenbeath 2-1 Clyde | William Hill Scottish Cup Second Round |
| 7 | 24/11/2018 | 1-0 v Brora RangersCowdenbeath 1-0 Brora Rangers | William Hill Scottish Cup Third Round |
| 8 | 29/12/2018 | 1-2 v Stirling AlbionStirling Albion 2-1 Cowdenbeath | Ladbrokes League Two |
| 9 | 5/1/2019 | 2-0 v Berwick RangersCowdenbeath 2-0 Berwick Rangers | Ladbrokes League Two |
| 10 | 12/1/2019 | 4-1 v Elgin CityElgin City 1-4 Cowdenbeath | Ladbrokes League Two |
| 11 | 26/1/2019 | 0-1 v ClydeClyde 1-0 Cowdenbeath | Ladbrokes League Two |
| 12 | 9/2/2019 | 1-1 v Queens ParkQueens Park 1-1 Cowdenbeath | Ladbrokes League Two |
| 13 | 16/2/2019 | 2-4 v Annan AthleticCowdenbeath 2-4 Annan Athletic | Ladbrokes League Two |
| 14 | 19/2/2019 | 1-0 v Albion RoversCowdenbeath 1-0 Albion Rovers | Ladbrokes League Two |
| 15 | 23/2/2019 | 0-2 v Edinburgh CityEdinburgh City 2-0 Cowdenbeath | Ladbrokes League Two |
| 16 | 2/3/2019 | 1-2 v Stirling AlbionCowdenbeath 1-2 Stirling Albion | Ladbrokes League Two |
| 17 | 5/3/2019 | 1-3 v PeterheadCowdenbeath 1-3 Peterhead | Ladbrokes League Two |
| 18 | 9/3/2019 | 1-1 v Berwick RangersBerwick Rangers 1-1 Cowdenbeath | Ladbrokes League Two |
| 19 | 23/3/2019 | 0-0 v Queens ParkCowdenbeath 0-0 Queens Park | Ladbrokes League Two |
| 20 | 26/3/2019 | 0-1 v Albion RoversAlbion Rovers 1-0 Cowdenbeath | Ladbrokes League Two |
| 21 | 30/3/2019 | 1-2 v PeterheadPeterhead 2-1 Cowdenbeath | Ladbrokes League Two |
| 22 | 6/4/2019 | 4-1 v Edinburgh CityCowdenbeath 4-1 Edinburgh City | Ladbrokes League Two |
| 23 | 13/4/2019 | 2-1 v Elgin CityCowdenbeath 2-1 Elgin City | Ladbrokes League Two |
| 24 | 20/4/2019 | 1-0 v Stirling AlbionStirling Albion 0-1 Cowdenbeath | Ladbrokes League Two |
| 25 | 27/4/2019 | 2-3 v Annan AthleticAnnan Athletic 3-2 Cowdenbeath | Ladbrokes League Two |
| 26 | 4/5/2019 | 2-1 v ClydeCowdenbeath 2-1 Clyde | Ladbrokes League Two |
