| 2000-08-12 | Ross CountyvClydeChampionship · Scotland | 0–2 | Championship · Scotland |
| 2000-08-05 | AyrvRoss CountyChampionship · Scotland | 1–0 | Championship · Scotland |
| 2000-05-06 | StenhousemuirvRoss CountyLeague One · Scotland | 2–2 | League One · Scotland |
| 2000-04-29 | Ross CountyvStranraerLeague One · Scotland | 3–1 | League One · Scotland |
| 2000-04-22 | HamiltonvRoss CountyLeague One · Scotland | 0–3 | League One · Scotland |
| 2000-04-15 | Queen of SthvRoss CountyLeague One · Scotland | 0–3 | League One · Scotland |
| 2000-04-08 | Ross CountyvPartickLeague One · Scotland | 1–3 | League One · Scotland |
| 2000-04-01 | Ross CountyvStirlingLeague One · Scotland | 5–1 | League One · Scotland |
| 2000-03-28 | Ross CountyvStenhousemuirLeague One · Scotland | 2–0 | League One · Scotland |
| 2000-03-25 | ArbroathvRoss CountyLeague One · Scotland | 1–2 | League One · Scotland |
| 2000-03-21 | StenhousemuirvRoss CountyLeague One · Scotland | 0–2 | League One · Scotland |
| 2000-03-18 | ClydevRoss CountyLeague One · Scotland | 0–0 | League One · Scotland |
| 2000-03-14 | AlloavRoss CountyLeague One · Scotland | 1–2 | League One · Scotland |
| 2000-03-11 | Ross CountyvAlloaLeague One · Scotland | 3–4 | League One · Scotland |
| 2000-03-07 | Ross CountyvClydeLeague One · Scotland | 2–2 | League One · Scotland |
| 2000-02-26 | StranraervRoss CountyLeague One · Scotland | 0–2 | League One · Scotland |
| 2000-02-19 | StirlingvRoss CountyLeague One · Scotland | 3–1 | League One · Scotland |
| 2000-02-12 | Ross CountyvArbroathLeague One · Scotland | 1–1 | League One · Scotland |
| 2000-02-05 | Ross CountyvQueen of SthLeague One · Scotland | 2–0 | League One · Scotland |
| 2000-01-29 | Ross CountyvHamiltonLeague One · Scotland | 0–1 | League One · Scotland |
| 2000-01-22 | PartickvRoss CountyLeague One · Scotland | 4–2 | League One · Scotland |
| 1999-12-04 | Ross CountyvPartickLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-11-27 | Queen of SthvRoss CountyLeague One · Scotland | 0–2 | League One · Scotland |
| 1999-11-20 | ArbroathvRoss CountyLeague One · Scotland | 0–1 | League One · Scotland |
| 1999-11-12 | Ross CountyvStirlingLeague One · Scotland | 1–3 | League One · Scotland |
| 1999-11-06 | ClydevRoss CountyLeague One · Scotland | 3–1 | League One · Scotland |
| 1999-10-30 | Ross CountyvAlloaLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-10-15 | Ross CountyvStranraerLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-10-09 | HamiltonvRoss CountyLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-10-02 | Ross CountyvQueen of SthLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-09-25 | PartickvRoss CountyLeague One · Scotland | 0–2 | League One · Scotland |
| 1999-09-18 | Ross CountyvClydeLeague One · Scotland | 2–0 | League One · Scotland |
| 1999-09-11 | AlloavRoss CountyLeague One · Scotland | 2–0 | League One · Scotland |
| 1999-09-04 | StirlingvRoss CountyLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-08-28 | Ross CountyvArbroathLeague One · Scotland | 2–0 | League One · Scotland |
| 1999-08-21 | Ross CountyvStenhousemuirLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-08-14 | StranraervRoss CountyLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-08-07 | Ross CountyvHamiltonLeague One · Scotland | 2–1 | League One · Scotland |
| 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 |