| 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 14 Aug 2018 | 1-3 v East FifeCowdenbeath 1-3 East Fife | IRN-BRU Cup First Round |
| 5 | Sat 20 Oct 2018 | 2-1 v ClydeCowdenbeath 2-1 Clyde | William Hill Scottish Cup Second Round |
| 6 | Sat 5 Jan 2019 | 2-0 v Berwick RangersCowdenbeath 2-0 Berwick Rangers | Ladbrokes League Two |
| 7 | Sat 23 Feb 2019 | 0-2 v Edinburgh CityEdinburgh City 2-0 Cowdenbeath | Ladbrokes League Two |
| 8 | Sat 2 Mar 2019 | 1-2 v Stirling AlbionCowdenbeath 1-2 Stirling Albion | Ladbrokes League Two |
| 9 | Tue 5 Mar 2019 | 1-3 v PeterheadCowdenbeath 1-3 Peterhead | Ladbrokes League Two |
| 10 | Sat 23 Mar 2019 | 0-0 v Queens ParkCowdenbeath 0-0 Queens Park | Ladbrokes League Two |
| 11 | Tue 26 Mar 2019 | 0-1 v Albion RoversAlbion Rovers 1-0 Cowdenbeath | Ladbrokes League Two |
| 12 | Sat 30 Mar 2019 | 1-2 v PeterheadPeterhead 2-1 Cowdenbeath | Ladbrokes League Two |
Football Web Pages