| 2021-12-22 | CowdenbeathvEdinburgh CityLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2021-12-18 | CowdenbeathvAlbion RvsLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2021-12-11 | StranraervCowdenbeathLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2021-12-04 | CowdenbeathvStirlingLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2021-11-20 | ForfarvCowdenbeathLeague Two · Scotland | 3–0 | League Two · Scotland |
| 2021-11-13 | ElginvCowdenbeathLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2021-11-06 | CowdenbeathvKelty HeartsLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2021-10-30 | Annan AthleticvCowdenbeathLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2021-10-16 | CowdenbeathvStenhousemuirLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2021-10-01 | Edinburgh CityvCowdenbeathLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2021-09-25 | StirlingvCowdenbeathLeague Two · Scotland | 4–0 | League Two · Scotland |
| 2021-09-18 | CowdenbeathvForfarLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2021-09-11 | Albion RvsvCowdenbeathLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2021-08-31 | CowdenbeathvStranraerLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2021-08-28 | CowdenbeathvAnnan AthleticLeague Two · Scotland | 1–3 | League Two · Scotland |
| 2021-08-21 | StenhousemuirvCowdenbeathLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2021-08-07 | CowdenbeathvElginLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2021-07-31 | Kelty HeartsvCowdenbeathLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2021-05-04 | CowdenbeathvAlbion RvsLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2021-05-01 | Annan AthleticvCowdenbeathLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2021-04-27 | CowdenbeathvBrechinLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2021-04-24 | StenhousemuirvCowdenbeathLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2021-04-20 | BrechinvCowdenbeathLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2021-04-17 | CowdenbeathvStirlingLeague Two · Scotland | 1–5 | League Two · Scotland |
| 2021-04-13 | Albion RvsvCowdenbeathLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2021-04-10 | CowdenbeathvElginLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2021-04-08 | StenhousemuirvCowdenbeathLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2021-04-06 | Queens ParkvCowdenbeathLeague Two · Scotland | 3–0 | League Two · Scotland |
| 2021-04-03 | CowdenbeathvAlbion RvsLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2021-03-30 | CowdenbeathvEdinburgh CityLeague Two · Scotland | 1–3 | League Two · Scotland |
| 2021-03-27 | CowdenbeathvStranraerLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2021-03-20 | Annan AthleticvCowdenbeathLeague Two · Scotland | 0–0 | League Two · Scotland |