| 1999-10-02 | CowdenbeathvAlbion RvsLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-09-25 | DumbartonvCowdenbeathLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-09-18 | CowdenbeathvEast FifeLeague Two · Scotland | 4–0 | League Two · Scotland |
| 1999-09-11 | BerwickvCowdenbeathLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-09-04 | CowdenbeathvBrechinLeague Two · Scotland | 6–1 | League Two · Scotland |
| 1999-08-28 | East StirlingvCowdenbeathLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1999-08-21 | Queens ParkvCowdenbeathLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-08-14 | CowdenbeathvForfarLeague Two · Scotland | 0–3 | League Two · Scotland |
| 1999-08-07 | MontrosevCowdenbeathLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1999-05-08 | MontrosevCowdenbeathLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-05-01 | CowdenbeathvStenhousemuirLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-04-24 | East StirlingvCowdenbeathLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-04-18 | BerwickvCowdenbeathLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-04-10 | CowdenbeathvDumbartonLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-04-05 | DumbartonvCowdenbeathLeague Two · Scotland | 6–1 | League Two · Scotland |
| 1999-04-03 | CowdenbeathvAlbion RvsLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-03-20 | Queens ParkvCowdenbeathLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-03-13 | CowdenbeathvRoss CountyLeague Two · Scotland | 2–3 | League Two · Scotland |
| 1999-03-06 | BrechinvCowdenbeathLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-02-27 | StenhousemuirvCowdenbeathLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-02-23 | Albion RvsvCowdenbeathLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-02-20 | CowdenbeathvMontroseLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-02-13 | CowdenbeathvBerwickLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-01-30 | CowdenbeathvQueens ParkLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-01-26 | CowdenbeathvBrechinLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1998-12-26 | Ross CountyvCowdenbeathLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1998-12-19 | CowdenbeathvEast StirlingLeague Two · Scotland | 3–2 | League Two · Scotland |
| 1998-12-12 | MontrosevCowdenbeathLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1998-11-28 | Queens ParkvCowdenbeathLeague Two · Scotland | 2–0 | League Two · Scotland |
| 1998-11-21 | CowdenbeathvAlbion RvsLeague Two · Scotland | 2–3 | League Two · Scotland |
| 1998-11-14 | BerwickvCowdenbeathLeague Two · Scotland | 3–1 | League Two · Scotland |
| 1998-11-07 | CowdenbeathvDumbartonLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1998-10-31 | BrechinvCowdenbeathLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1998-10-28 | CowdenbeathvRoss CountyLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1998-10-17 | East StirlingvCowdenbeathLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1998-10-09 | CowdenbeathvStenhousemuirLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1998-10-03 | CowdenbeathvQueens ParkLeague Two · Scotland | 0–3 | League Two · Scotland |
| 1998-09-26 | Albion RvsvCowdenbeathLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1998-09-19 | DumbartonvCowdenbeathLeague Two · Scotland | 5–0 | League Two · Scotland |
| 1998-09-12 | CowdenbeathvBerwickLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1998-09-05 | CowdenbeathvBrechinLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1998-08-29 | Ross CountyvCowdenbeathLeague Two · Scotland | 2–0 | League Two · Scotland |
| 1998-08-22 | CowdenbeathvEast StirlingLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1998-08-15 | StenhousemuirvCowdenbeathLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1998-08-04 | CowdenbeathvMontroseLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1998-05-09 | DumbartonvCowdenbeathLeague Two · Scotland | 2–3 | League Two · Scotland |
| 1998-05-02 | CowdenbeathvAlloaLeague Two · Scotland | 1–3 | League Two · Scotland |
| 1998-04-25 | Ross CountyvCowdenbeathLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1998-04-18 | East StirlingvCowdenbeathLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1998-04-11 | CowdenbeathvMontroseLeague Two · Scotland | 0–0 | League Two · Scotland |