| 2009-05-09 | East StirlingvCowdenbeathLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2009-05-02 | CowdenbeathvForfarLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2009-04-25 | MontrosevCowdenbeathLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2009-04-18 | CowdenbeathvDumbartonLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2009-04-11 | Albion RvsvCowdenbeathLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2009-04-04 | CowdenbeathvElginLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2009-03-31 | ForfarvCowdenbeathLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2009-03-21 | CowdenbeathvEast StirlingLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2009-03-17 | CowdenbeathvMontroseLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2009-03-14 | Annan AthleticvCowdenbeathLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2009-03-10 | CowdenbeathvForfarLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2009-03-07 | BerwickvCowdenbeathLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2009-03-03 | StenhousemuirvCowdenbeathLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2009-02-28 | CowdenbeathvStenhousemuirLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2009-02-21 | DumbartonvCowdenbeathLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2009-01-31 | CowdenbeathvAnnan AthleticLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2009-01-24 | CowdenbeathvAlbion RvsLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2009-01-17 | ElginvCowdenbeathLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2009-01-13 | CowdenbeathvBerwickLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2009-01-10 | CowdenbeathvDumbartonLeague Two · Scotland | 2–0 | League Two · Scotland |