| 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 |