| 2016-12-31 | StirlingvCowdenbeathLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2016-12-24 | CowdenbeathvArbroathLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2016-12-17 | CowdenbeathvForfarLeague Two · Scotland | 3–4 | League Two · Scotland |
| 2016-12-10 | Annan AthleticvCowdenbeathLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2016-12-03 | CowdenbeathvClydeLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2016-11-19 | Edinburgh CityvCowdenbeathLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2016-11-12 | CowdenbeathvMontroseLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2016-11-05 | BerwickvCowdenbeathLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2016-10-29 | ElginvCowdenbeathLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2016-10-15 | CowdenbeathvAnnan AthleticLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2016-10-01 | CowdenbeathvStirlingLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2016-09-24 | ArbroathvCowdenbeathLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2016-09-17 | CowdenbeathvBerwickLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2016-09-10 | MontrosevCowdenbeathLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2016-08-27 | ClydevCowdenbeathLeague Two · Scotland | 5–3 | League Two · Scotland |
| 2016-08-20 | CowdenbeathvEdinburgh CityLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2016-08-13 | ForfarvCowdenbeathLeague Two · Scotland | 4–3 | League Two · Scotland |
| 2016-08-06 | CowdenbeathvElginLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2016-04-30 | StranraervCowdenbeathLeague One · Scotland | 1–0 | League One · Scotland |
| 2016-04-23 | CowdenbeathvStenhousemuirLeague One · Scotland | 1–3 | League One · Scotland |
| 2016-04-16 | Albion RvsvCowdenbeathLeague One · Scotland | 0–0 | League One · Scotland |
| 2016-04-09 | CowdenbeathvBrechinLeague One · Scotland | 2–1 | League One · Scotland |
| 2016-04-02 | CowdenbeathvAyrLeague One · Scotland | 1–0 | League One · Scotland |
| 2016-03-26 | PeterheadvCowdenbeathLeague One · Scotland | 0–1 | League One · Scotland |
| 2016-03-19 | CowdenbeathvDunfermlineLeague One · Scotland | 0–1 | League One · Scotland |
| 2016-03-12 | ForfarvCowdenbeathLeague One · Scotland | 1–1 | League One · Scotland |
| 2016-03-05 | CowdenbeathvAirdrie UtdLeague One · Scotland | 1–3 | League One · Scotland |
| 2016-03-01 | AyrvCowdenbeathLeague One · Scotland | 4–1 | League One · Scotland |
| 2016-02-27 | StenhousemuirvCowdenbeathLeague One · Scotland | 2–3 | League One · Scotland |
| 2016-02-23 | CowdenbeathvForfarLeague One · Scotland | 1–4 | League One · Scotland |
| 2016-02-20 | CowdenbeathvPeterheadLeague One · Scotland | 2–3 | League One · Scotland |
| 2016-02-13 | BrechinvCowdenbeathLeague One · Scotland | 2–2 | League One · Scotland |
| 2016-02-09 | CowdenbeathvAlbion RvsLeague One · Scotland | 1–2 | League One · Scotland |
| 2016-02-06 | Airdrie UtdvCowdenbeathLeague One · Scotland | 2–0 | League One · Scotland |
| 2016-01-23 | CowdenbeathvStranraerLeague One · Scotland | 0–2 | League One · Scotland |
| 2016-01-02 | DunfermlinevCowdenbeathLeague One · Scotland | 2–1 | League One · Scotland |