| 1999-05-08 | East StirlingvRoss CountyLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-05-01 | Ross CountyvAlbion RvsLeague Two · Scotland | 2–0 | League Two · Scotland |
| 1999-04-24 | MontrosevRoss CountyLeague Two · Scotland | 2–3 | League Two · Scotland |
| 1999-04-17 | Ross CountyvQueens ParkLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-04-10 | StenhousemuirvRoss CountyLeague Two · Scotland | 3–2 | League Two · Scotland |
| 1999-04-03 | BrechinvRoss CountyLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1999-03-20 | Ross CountyvDumbartonLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1999-03-13 | CowdenbeathvRoss CountyLeague Two · Scotland | 2–3 | League Two · Scotland |
| 1999-03-09 | Ross CountyvBrechinLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1999-03-06 | Ross CountyvBerwickLeague Two · Scotland | 6–0 | League Two · Scotland |
| 1999-03-02 | Ross CountyvEast StirlingLeague Two · Scotland | 4–2 | League Two · Scotland |
| 1999-02-27 | Albion RvsvRoss CountyLeague Two · Scotland | 3–3 | 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 |
| 1999-01-30 | DumbartonvRoss CountyLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1999-01-27 | BerwickvRoss CountyLeague Two · Scotland | 2–2 | League Two · Scotland |
| 1998-12-26 | Ross CountyvCowdenbeathLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1998-12-19 | Ross CountyvMontroseLeague Two · Scotland | 3–0 | League Two · Scotland |
| 1998-12-12 | East StirlingvRoss CountyLeague Two · Scotland | 2–2 | League Two · Scotland |
| 1998-11-28 | Ross CountyvDumbartonLeague Two · Scotland | 2–0 | League Two · Scotland |
| 1998-11-21 | BrechinvRoss CountyLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1998-11-14 | Ross CountyvQueens ParkLeague Two · Scotland | 5–1 | League Two · Scotland |
| 1998-11-07 | StenhousemuirvRoss CountyLeague Two · Scotland | 2–4 | League Two · Scotland |
| 1998-10-31 | Ross CountyvBerwickLeague Two · Scotland | 3–1 | League Two · Scotland |
| 1998-10-28 | CowdenbeathvRoss CountyLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1998-10-17 | MontrosevRoss CountyLeague Two · Scotland | 3–6 | League Two · Scotland |
| 1998-10-10 | Ross CountyvAlbion RvsLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1998-10-03 | DumbartonvRoss CountyLeague Two · Scotland | 1–2 | League Two · Scotland |
| 1998-09-26 | Ross CountyvBrechinLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1998-09-19 | Ross CountyvStenhousemuirLeague Two · Scotland | 0–1 | League Two · Scotland |
| 1998-09-12 | Queens ParkvRoss CountyLeague Two · Scotland | 4–2 | League Two · Scotland |
| 1998-09-05 | BerwickvRoss CountyLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1998-08-29 | Ross CountyvCowdenbeathLeague Two · Scotland | 2–0 | League Two · Scotland |
| 1998-08-22 | Ross CountyvMontroseLeague Two · Scotland | 3–1 | League Two · Scotland |
| 1998-08-15 | Albion RvsvRoss CountyLeague Two · Scotland | 0–8 | League Two · Scotland |
| 1998-08-04 | Ross CountyvEast StirlingLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1998-05-09 | Ross CountyvEast StirlingLeague Two · Scotland | 5–2 | League Two · Scotland |
| 1998-05-02 | Queens ParkvRoss CountyLeague Two · Scotland | 0–4 | League Two · Scotland |
| 1998-04-25 | Ross CountyvCowdenbeathLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1998-04-18 | Ross CountyvArbroathLeague Two · Scotland | 1–0 | League Two · Scotland |
| 1998-04-11 | Albion RvsvRoss CountyLeague Two · Scotland | 1–3 | League Two · Scotland |
| 1998-04-04 | AlloavRoss CountyLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1998-03-28 | Ross CountyvDumbartonLeague Two · Scotland | 0–0 | League Two · Scotland |
| 1998-03-24 | Ross CountyvAlloaLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1998-03-21 | BerwickvRoss CountyLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1998-03-17 | Ross CountyvAlbion RvsLeague Two · Scotland | 6–2 | League Two · Scotland |
| 1998-03-14 | Ross CountyvMontroseLeague Two · Scotland | 2–1 | League Two · Scotland |
| 1998-03-10 | MontrosevRoss CountyLeague Two · Scotland | 0–2 | League Two · Scotland |
| 1998-03-07 | ArbroathvRoss CountyLeague Two · Scotland | 1–1 | League Two · Scotland |
| 1998-02-21 | East StirlingvRoss CountyLeague Two · Scotland | 1–0 | League Two · Scotland |