| 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 |