| 1 | Sat 6 Aug 2016 | 10-1 v Elgin CityCowdenbeath 0-1 Elgin City | Ladbrokes League Two |
| 2 | Sat 13 Aug 2016 | 13-4 v Forfar AthleticForfar Athletic 4-3 Cowdenbeath | Ladbrokes League Two |
| 3 | Sat 20 Aug 2016 | 12-0 v Edinburgh CityCowdenbeath 2-0 Edinburgh City | Ladbrokes League Two |
| 4 | Sat 27 Aug 2016 | 13-5 v ClydeClyde 5-3 Cowdenbeath | Ladbrokes League Two |
| 5 | Sat 10 Sep 2016 | 12-1 v MontroseMontrose 1-2 Cowdenbeath | Ladbrokes League Two |
| 6 | Sat 17 Sep 2016 | 10-2 v Berwick RangersCowdenbeath 0-2 Berwick Rangers | Ladbrokes League Two |
| 7 | Sat 24 Sep 2016 | 10-0 v ArbroathArbroath 0-0 Cowdenbeath | Ladbrokes League Two |
| 8 | Sat 1 Oct 2016 | 10-2 v Stirling AlbionCowdenbeath 0-2 Stirling Albion | Ladbrokes League Two |
| 9 | Sat 15 Oct 2016 | 12-2 v Annan AthleticCowdenbeath 2-2 Annan Athletic | Ladbrokes League Two |
| 10 | Sat 29 Oct 2016 | 11-3 v Elgin CityElgin City 3-1 Cowdenbeath | Ladbrokes League Two |
| 11 | Sat 5 Nov 2016 | 11-1 v Berwick RangersBerwick Rangers 1-1 Cowdenbeath | Ladbrokes League Two |
| 12 | Sat 12 Nov 2016 | 12-0 v MontroseCowdenbeath 2-0 Montrose | Ladbrokes League Two |
| 13 | Sat 19 Nov 2016 | 11-1 v Edinburgh CityEdinburgh City 1-1 Cowdenbeath | Ladbrokes League Two |
| 14 | Sat 3 Dec 2016 | 11-0 v ClydeCowdenbeath 1-0 Clyde | Ladbrokes League Two |
| 15 | Sat 10 Dec 2016 | 10-2 v Annan AthleticAnnan Athletic 2-0 Cowdenbeath | Ladbrokes League Two |
| 16 | Sat 17 Dec 2016 | 13-4 v Forfar AthleticCowdenbeath 3-4 Forfar Athletic | Ladbrokes League Two |
| 17 | Sat 24 Dec 2016 | 10-2 v ArbroathCowdenbeath 0-2 Arbroath | Ladbrokes League Two |
| 18 | Sat 31 Dec 2016 | 12-1 v Stirling AlbionStirling Albion 1-2 Cowdenbeath | Ladbrokes League Two |
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