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