| 1 | Tue 10 Jul 2018 | 190-4 v St JohnstoneBerwick Rangers 0-4 St Johnstone | Friendly |
| 2 | Tue 17 Jul 2018 | 190-4 v Annan AthleticAnnan Athletic 4-0 Berwick Rangers | Betfred Cup Group F |
| 3 | Sat 21 Jul 2018 | 190-3 v AirdrieoniansBerwick Rangers 0-3 Airdrieonians | Betfred Cup Group F |
| 4 | Tue 24 Jul 2018 | 190-4 v Hamilton AcademicalBerwick Rangers 0-4 Hamilton Academical | Betfred Cup Group F |
| 5 | Tue 14 Aug 2018 | 190-3 v AirdrieoniansBerwick Rangers 0-3 Airdrieonians | IRN-BRU Cup First Round |
| 6 | Sat 16 Feb 2019 | 2-4 v Annan AthleticCowdenbeath 2-4 Annan Athletic | Ladbrokes League Two |
| 7 | Tue 19 Feb 2019 | 1-0 v Albion RoversCowdenbeath 1-0 Albion Rovers | Ladbrokes League Two |
| 8 | Sat 23 Feb 2019 | 0-2 v Edinburgh CityEdinburgh City 2-0 Cowdenbeath | Ladbrokes League Two |
| 9 | Tue 26 Feb 2019 | 0-1 v PeterheadPeterhead 1-0 Cowdenbeath | Ladbrokes League Two |
| 10 | Tue 5 Mar 2019 | 1-3 v PeterheadCowdenbeath 1-3 Peterhead | Ladbrokes League Two |
| 11 | Sat 9 Mar 2019 | 1-1 v Berwick RangersBerwick Rangers 1-1 Cowdenbeath | Ladbrokes League Two |
| 12 | Tue 26 Mar 2019 | 0-1 v Albion RoversAlbion Rovers 1-0 Cowdenbeath | Ladbrokes League Two |
| 13 | Sat 30 Mar 2019 | 1-2 v PeterheadPeterhead 2-1 Cowdenbeath | Ladbrokes League Two |
| 14 | Sat 6 Apr 2019 | 4-1 v Edinburgh CityCowdenbeath 4-1 Edinburgh City | Ladbrokes League Two |
| 15 | Sat 13 Apr 2019 | 2-1 v Elgin CityCowdenbeath 2-1 Elgin City | Ladbrokes League Two |
| 16 | Sat 20 Apr 2019 | 1-0 v Stirling AlbionStirling Albion 0-1 Cowdenbeath | Ladbrokes League Two |
| 17 | Sat 27 Apr 2019 | 2-3 v Annan AthleticAnnan Athletic 3-2 Cowdenbeath | Ladbrokes League Two |
| 18 | Sat 4 May 2019 | 2-1 v ClydeCowdenbeath 2-1 Clyde | Ladbrokes League Two |
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