| 1999-12-27 | Inverness CvClydebankChampionship · Scotland | 4–1 | Championship · Scotland |
| 1999-12-18 | DunfermlinevInverness CChampionship · Scotland | 1–0 | Championship · Scotland |
| 1999-12-11 | Inverness CvSt MirrenChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-12-04 | Raith RvsvInverness CChampionship · Scotland | 4–2 | Championship · Scotland |
| 1999-11-30 | Inverness CvAyrChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-11-27 | Inverness CvAirdrieChampionship · Scotland | 2–0 | Championship · Scotland |
| 1999-11-12 | MortonvInverness CChampionship · Scotland | 5–1 | Championship · Scotland |
| 1999-11-06 | Inverness CvLivingstonChampionship · Scotland | 2–0 | Championship · Scotland |
| 1999-10-30 | ClydebankvInverness CChampionship · Scotland | 0–3 | Championship · Scotland |
| 1999-10-23 | Inverness CvDunfermlineChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-10-16 | FalkirkvInverness CChampionship · Scotland | 0–2 | Championship · Scotland |
| 1999-10-02 | AirdrievInverness CChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-09-25 | Inverness CvRaith RvsChampionship · Scotland | 0–2 | Championship · Scotland |
| 1999-09-18 | LivingstonvInverness CChampionship · Scotland | 2–2 | Championship · Scotland |
| 1999-09-11 | Inverness CvClydebankChampionship · Scotland | 1–0 | Championship · Scotland |
| 1999-09-04 | Inverness CvMortonChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-08-28 | AyrvInverness CChampionship · Scotland | 1–0 | Championship · Scotland |
| 1999-08-21 | St MirrenvInverness CChampionship · Scotland | 3–2 | Championship · Scotland |
| 1999-08-14 | Inverness CvFalkirkChampionship · Scotland | 2–3 | Championship · Scotland |
| 1999-08-07 | DunfermlinevInverness CChampionship · Scotland | 4–0 | Championship · Scotland |
| 1999-05-08 | Inverness CvAlloaLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-05-01 | LivingstonvInverness CLeague One · Scotland | 4–3 | League One · Scotland |
| 1999-04-24 | Inverness CvPartickLeague One · Scotland | 3–2 | League One · Scotland |
| 1999-04-17 | Queen of SthvInverness CLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-04-10 | Inverness CvStirlingLeague One · Scotland | 2–2 | League One · Scotland |
| 1999-04-03 | Inverness CvClydeLeague One · Scotland | 3–0 | League One · Scotland |
| 1999-03-20 | ForfarvInverness CLeague One · Scotland | 0–3 | League One · Scotland |
| 1999-03-13 | Inverness CvEast FifeLeague One · Scotland | 4–0 | League One · Scotland |
| 1999-03-06 | ArbroathvInverness CLeague One · Scotland | 3–1 | League One · Scotland |
| 1999-02-27 | Inverness CvLivingstonLeague One · Scotland | 3–1 | League One · Scotland |
| 1999-02-20 | AlloavInverness CLeague One · Scotland | 1–4 | League One · Scotland |
| 1999-02-13 | Inverness CvQueen of SthLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-02-06 | StirlingvInverness CLeague One · Scotland | 1–5 | League One · Scotland |
| 1999-01-30 | Inverness CvForfarLeague One · Scotland | 2–0 | League One · Scotland |
| 1999-01-16 | ClydevInverness CLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-01-09 | Inverness CvArbroathLeague One · Scotland | 2–0 | League One · Scotland |