| 1999-12-22 | CowdenbeathvQueens ParkLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-12-18 | Queens ParkvEast StirlingLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1999-12-04 | Queens ParkvEast FifeLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1999-11-27 | MontrosevQueens ParkLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-11-20 | Queens ParkvBerwickLeague Two · Scotland | 1–4 | League Two · Scotland |
| 1999-11-14 | ForfarvQueens ParkLeague Two · Scotland | 2–2 | League Two · Scotland |
| 1999-11-06 | Albion RvsvQueens ParkLeague Two · Scotland | 2–4 | League Two · Scotland |
| 1999-10-30 | Queens ParkvDumbartonLeague Two · Scotland | 3–2 | League Two · Scotland |
| 1999-10-23 | East StirlingvQueens ParkLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-10-16 | Queens ParkvBrechinLeague Two · Scotland | 5–3 | League Two · Scotland |
| 1999-10-02 | Queens ParkvMontroseLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-09-25 | East FifevQueens ParkLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-09-18 | Queens ParkvAlbion RvsLeague Two · Scotland | 2–0 | League Two · Scotland |
| 1999-09-11 | DumbartonvQueens ParkLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1999-09-04 | Queens ParkvForfarLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-08-28 | BerwickvQueens ParkLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-08-21 | Queens ParkvCowdenbeathLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-08-14 | BrechinvQueens ParkLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-08-07 | Queens ParkvEast StirlingLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-05-08 | Queens ParkvBerwickLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-05-01 | DumbartonvQueens ParkLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1999-04-24 | Queens ParkvBrechinLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-04-17 | Ross CountyvQueens ParkLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-04-10 | Queens ParkvMontroseLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-04-03 | Queens ParkvEast StirlingLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-03-20 | Queens ParkvCowdenbeathLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-03-13 | Queens ParkvAlbion RvsLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-03-06 | StenhousemuirvQueens ParkLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-02-27 | Queens ParkvDumbartonLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-02-20 | BerwickvQueens ParkLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-02-13 | Queens ParkvRoss CountyLeague Two · Scotland | 0–3 | League Two · Scotland |
| 1999-02-06 | MontrosevQueens ParkLeague Two · Scotland | 3–0 | League Two · Scotland |
| 1999-01-30 | CowdenbeathvQueens ParkLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-01-26 | Queens ParkvStenhousemuirLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-01-16 | East StirlingvQueens ParkLeague Two · Scotland | 1–1 | League Two · Scotland |