| 2008-12-20 | East StirlingvCowdenbeathLeague Two · Scotland | 1–4 | League Two · Scotland |
| 2008-12-13 | MontrosevCowdenbeathLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2008-11-22 | BerwickvCowdenbeathLeague Two · Scotland | 2–3 | League Two · Scotland |
| 2008-11-15 | CowdenbeathvStenhousemuirLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2008-11-08 | CowdenbeathvElginLeague Two · Scotland | 4–1 | League Two · Scotland |
| 2008-11-01 | Albion RvsvCowdenbeathLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2008-10-18 | Annan AthleticvCowdenbeathLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2008-10-04 | CowdenbeathvEast StirlingLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2008-09-27 | CowdenbeathvMontroseLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2008-09-20 | DumbartonvCowdenbeathLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2008-09-13 | CowdenbeathvBerwickLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2008-08-30 | StenhousemuirvCowdenbeathLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2008-08-23 | ElginvCowdenbeathLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2008-08-16 | CowdenbeathvAlbion RvsLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2008-08-09 | ForfarvCowdenbeathLeague Two · Scotland | 0–1 | League Two · Scotland |
| 2008-08-02 | CowdenbeathvAnnan AthleticLeague Two · Scotland | 1–4 | League Two · Scotland |
| 2008-04-26 | CowdenbeathvQueens ParkLeague One · Scotland | 1–0 | League One · Scotland |
| 2008-04-19 | Ross CountyvCowdenbeathLeague One · Scotland | 3–0 | League One · Scotland |
| 2008-04-15 | Airdrie UtdvCowdenbeathLeague One · Scotland | 4–0 | League One · Scotland |
| 2008-04-05 | CowdenbeathvAlloaLeague One · Scotland | 1–1 | League One · Scotland |
| 2008-04-01 | Queens ParkvCowdenbeathLeague One · Scotland | 2–3 | League One · Scotland |
| 2008-03-29 | CowdenbeathvBrechinLeague One · Scotland | 0–2 | League One · Scotland |
| 2008-03-22 | AyrvCowdenbeathLeague One · Scotland | 1–1 | League One · Scotland |
| 2008-03-18 | CowdenbeathvQueens ParkLeague One · Scotland | 2–4 | League One · Scotland |
| 2008-03-15 | CowdenbeathvBerwickLeague One · Scotland | 1–2 | League One · Scotland |
| 2008-03-11 | BerwickvCowdenbeathLeague One · Scotland | 4–5 | League One · Scotland |
| 2008-03-04 | Ross CountyvCowdenbeathLeague One · Scotland | 4–1 | League One · Scotland |
| 2008-03-01 | Raith RvsvCowdenbeathLeague One · Scotland | 3–2 | League One · Scotland |
| 2008-02-23 | CowdenbeathvPeterheadLeague One · Scotland | 0–4 | League One · Scotland |
| 2008-02-16 | AlloavCowdenbeathLeague One · Scotland | 3–2 | League One · Scotland |
| 2008-02-09 | CowdenbeathvAirdrie UtdLeague One · Scotland | 0–1 | League One · Scotland |
| 2008-01-26 | CowdenbeathvRoss CountyLeague One · Scotland | 2–4 | League One · Scotland |
| 2008-01-19 | BrechinvCowdenbeathLeague One · Scotland | 0–1 | League One · Scotland |
| 2008-01-05 | CowdenbeathvAyrLeague One · Scotland | 2–0 | League One · Scotland |
| 2008-01-02 | CowdenbeathvRaith RvsLeague One · Scotland | 1–4 | League One · Scotland |