| 1999-04-24 | StenhousemuirvDumbartonLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-04-24 | East StirlingvCowdenbeathLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-04-24 | Queens ParkvBrechinLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-04-24 | Albion RvsvBerwickLeague Two · Scotland | 0–3 | League Two · Scotland |
| 1999-04-24 | MontrosevRoss CountyLeague Two · Scotland | 2–3 | League Two · Scotland |
| 1999-04-18 | BerwickvCowdenbeathLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-04-17 | Albion RvsvEast StirlingLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-04-17 | DumbartonvBrechinLeague Two · Scotland | 2–0 | League Two · Scotland |
| 1999-04-17 | Ross CountyvQueens ParkLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-04-17 | MontrosevStenhousemuirLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-04-10 | BrechinvAlbion RvsLeague Two · Scotland | 3–1 | League Two · Scotland |
| 1999-04-10 | East StirlingvBerwickLeague Two · Scotland | 3–3 | League Two · Scotland |
| 1999-04-10 | Queens ParkvMontroseLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-04-10 | CowdenbeathvDumbartonLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-04-10 | StenhousemuirvRoss CountyLeague Two · Scotland | 3–2 | League Two · Scotland |
| 1999-04-05 | DumbartonvCowdenbeathLeague Two · Scotland | 6–1 | League Two · Scotland |
| 1999-04-03 | BrechinvRoss CountyLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1999-04-03 | DumbartonvMontroseLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-04-03 | StenhousemuirvBerwickLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-04-03 | CowdenbeathvAlbion RvsLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-04-03 | Queens ParkvEast StirlingLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-03-20 | BerwickvBrechinLeague Two · Scotland | 2–3 | League Two · Scotland |
| 1999-03-20 | Ross CountyvDumbartonLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-03-20 | Queens ParkvCowdenbeathLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-03-20 | Albion RvsvStenhousemuirLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-03-20 | MontrosevEast StirlingLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-03-16 | Albion RvsvMontroseLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-03-13 | BerwickvDumbartonLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1999-03-13 | Queens ParkvAlbion RvsLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-03-13 | CowdenbeathvRoss CountyLeague Two · Scotland | 2–3 | League Two · Scotland |
| 1999-03-13 | MontrosevBrechinLeague Two · Scotland | 1–3 | League Two · Scotland |
| 1999-03-13 | East StirlingvStenhousemuirLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-03-09 | Ross CountyvBrechinLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-03-09 | DumbartonvAlbion RvsLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-03-06 | Ross CountyvBerwickLeague Two · Scotland | 6–0 | League Two · Scotland |
| 1999-03-06 | StenhousemuirvQueens ParkLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-03-06 | DumbartonvEast StirlingLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-03-06 | BrechinvCowdenbeathLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-03-02 | Ross CountyvEast StirlingLeague Two · Scotland | 4–2 | League Two · Scotland |
| 1999-02-27 | StenhousemuirvCowdenbeathLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-02-27 | Albion RvsvRoss CountyLeague Two · Scotland | 3–3 | League Two · Scotland |
| 1999-02-27 | East StirlingvBrechinLeague Two · Scotland | 4–1 | League Two · Scotland |
| 1999-02-27 | Queens ParkvDumbartonLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-02-27 | MontrosevBerwickLeague Two · Scotland | 0–3 | League Two · Scotland |
| 1999-02-23 | Albion RvsvCowdenbeathLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1999-02-23 | StenhousemuirvMontroseLeague Two · Scotland | 3–1 | League Two · Scotland |
| 1999-02-20 | CowdenbeathvMontroseLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1999-02-20 | BrechinvStenhousemuirLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-02-20 | BerwickvQueens ParkLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1999-02-16 | East StirlingvAlbion RvsLeague Two · Scotland | 4–1 | League Two · Scotland |