| 2001-03-10 | ElginvCowdenbeathLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2001-03-07 | DumbartonvCowdenbeathLeague Two · Scotland | 3–0 | League Two · Scotland |
| 2001-02-24 | CowdenbeathvAlbion RvsLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2001-02-17 | BrechinvCowdenbeathLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2001-01-02 | East FifevCowdenbeathLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2000-12-23 | CowdenbeathvBrechinLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2000-12-02 | MontrosevCowdenbeathLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2000-11-25 | CowdenbeathvPeterheadLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2000-11-18 | HamiltonvCowdenbeathLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2000-11-11 | CowdenbeathvDumbartonLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2000-11-04 | CowdenbeathvEast FifeLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2000-10-28 | ElginvCowdenbeathLeague Two · Scotland | 2–3 | League Two · Scotland |
| 2000-10-21 | Albion RvsvCowdenbeathLeague Two · Scotland | 1–0 | League Two · Scotland |
| 2000-10-14 | CowdenbeathvEast StirlingLeague Two · Scotland | 3–0 | League Two · Scotland |
| 2000-10-07 | PeterheadvCowdenbeathLeague Two · Scotland | 3–0 | League Two · Scotland |
| 2000-09-30 | CowdenbeathvMontroseLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2000-09-23 | DumbartonvCowdenbeathLeague Two · Scotland | 2–4 | League Two · Scotland |
| 2000-09-16 | CowdenbeathvHamiltonLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2000-09-09 | East FifevCowdenbeathLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2000-08-26 | CowdenbeathvElginLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2000-08-19 | BrechinvCowdenbeathLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2000-08-12 | CowdenbeathvAlbion RvsLeague Two · Scotland | 5–0 | League Two · Scotland |
| 2000-08-05 | East StirlingvCowdenbeathLeague Two · Scotland | 0–2 | League Two · Scotland |
| 2000-05-06 | CowdenbeathvQueens ParkLeague Two · Scotland | 2–3 | League Two · Scotland |
| 2000-04-29 | ForfarvCowdenbeathLeague Two · Scotland | 2–2 | League Two · Scotland |
| 2000-04-22 | CowdenbeathvMontroseLeague Two · Scotland | 2–1 | League Two · Scotland |
| 2000-04-15 | Albion RvsvCowdenbeathLeague Two · Scotland | 0–3 | League Two · Scotland |
| 2000-04-08 | CowdenbeathvDumbartonLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2000-04-01 | BrechinvCowdenbeathLeague Two · Scotland | 1–2 | League Two · Scotland |
| 2000-03-25 | CowdenbeathvEast StirlingLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2000-03-18 | East FifevCowdenbeathLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2000-03-11 | CowdenbeathvBerwickLeague Two · Scotland | 1–3 | League Two · Scotland |
| 2000-03-04 | Queens ParkvCowdenbeathLeague Two · Scotland | 3–1 | League Two · Scotland |
| 2000-02-26 | CowdenbeathvForfarLeague Two · Scotland | 4–1 | League Two · Scotland |
| 2000-02-19 | CowdenbeathvBrechinLeague Two · Scotland | 1–1 | League Two · Scotland |
| 2000-02-12 | East StirlingvCowdenbeathLeague Two · Scotland | 0–4 | League Two · Scotland |
| 2000-02-05 | CowdenbeathvAlbion RvsLeague Two · Scotland | 5–0 | League Two · Scotland |
| 2000-01-22 | DumbartonvCowdenbeathLeague Two · Scotland | 2–0 | League Two · Scotland |
| 2000-01-15 | BerwickvCowdenbeathLeague Two · Scotland | 0–0 | League Two · Scotland |
| 2000-01-03 | CowdenbeathvEast FifeLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-12-22 | CowdenbeathvQueens ParkLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-12-18 | MontrosevCowdenbeathLeague Two · Scotland | 1–3 | League Two · Scotland |
| 1999-12-08 | CowdenbeathvDumbartonLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-11-27 | Albion RvsvCowdenbeathLeague Two · Scotland | 1–4 | League Two · Scotland |
| 1999-11-20 | CowdenbeathvEast StirlingLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-11-14 | BrechinvCowdenbeathLeague Two · Scotland | 2–0 | League Two · Scotland |
| 1999-11-06 | East FifevCowdenbeathLeague Two · Scotland | 2–3 | League Two · Scotland |
| 1999-10-30 | CowdenbeathvBerwickLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-10-23 | CowdenbeathvMontroseLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-10-16 | ForfarvCowdenbeathLeague Two · Scotland | 3–1 | League Two · Scotland |