| 1999-02-16 | BrechinvMontroseLeague Two · Scotland | 2–3 | League Two · Scotland |
| 1999-02-13 | BrechinvDumbartonLeague Two · Scotland | 3–3 | League Two · Scotland |
| 1999-02-13 | CowdenbeathvBerwickLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-02-13 | Queens ParkvRoss CountyLeague Two · Scotland | 0–3 | League Two · Scotland |
| 1999-02-06 | Ross CountyvStenhousemuirLeague Two · Scotland | 2–2 | League Two · Scotland |
| 1999-02-06 | BerwickvEast StirlingLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-02-06 | MontrosevQueens ParkLeague Two · Scotland | 3–0 | League Two · Scotland |
| 1999-02-06 | Albion RvsvBrechinLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-02-02 | DumbartonvBerwickLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-01-30 | StenhousemuirvAlbion RvsLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-01-30 | DumbartonvRoss CountyLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-01-30 | CowdenbeathvQueens ParkLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-01-30 | BrechinvBerwickLeague Two · Scotland | 0–3 | League Two · Scotland |
| 1999-01-30 | East StirlingvMontroseLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-01-27 | BerwickvRoss CountyLeague Two · Scotland | 2–2 | League Two · Scotland |
| 1999-01-26 | CowdenbeathvBrechinLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-01-26 | East StirlingvDumbartonLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-01-26 | Queens ParkvStenhousemuirLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-01-16 | MontrosevDumbartonLeague Two · Scotland | 4–2 | League Two · Scotland |
| 1999-01-16 | BerwickvStenhousemuirLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-01-16 | East StirlingvQueens ParkLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-01-09 | MontrosevAlbion RvsLeague Two · Scotland | 2–3 | League Two · Scotland |