| 1999-10-16 | MotherwellvHibernianPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-10-02 | AberdeenvHibernianPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-09-25 | HibernianvCelticPremiership · Scotland | 0–2 | Premiership · Scotland |
| 1999-09-19 | HibernianvKilmarnockPremiership · Scotland | 0–3 | Premiership · Scotland |
| 1999-09-11 | Dundee UnitedvHibernianPremiership · Scotland | 3–1 | Premiership · Scotland |
| 1999-08-28 | HibernianvRangersPremiership · Scotland | 0–1 | Premiership · Scotland |
| 1999-08-21 | St JohnstonevHibernianPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-08-14 | HibernianvHeartsPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1999-08-08 | DundeevHibernianPremiership · Scotland | 3–4 | Premiership · Scotland |
| 1999-07-31 | HibernianvMotherwellPremiership · Scotland | 2–2 | Premiership · Scotland |
| 1999-05-08 | HibernianvFalkirkChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-05-01 | StranraervHibernianChampionship · Scotland | 0–4 | Championship · Scotland |
| 1999-04-24 | HibernianvMortonChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-04-17 | HibernianvSt MirrenChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-04-10 | Raith RvsvHibernianChampionship · Scotland | 1–3 | Championship · Scotland |
| 1999-04-03 | HamiltonvHibernianChampionship · Scotland | 0–2 | Championship · Scotland |
| 1999-03-20 | HibernianvAirdrieChampionship · Scotland | 3–0 | Championship · Scotland |
| 1999-03-13 | ClydebankvHibernianChampionship · Scotland | 2–0 | Championship · Scotland |
| 1999-02-27 | AyrvHibernianChampionship · Scotland | 1–3 | Championship · Scotland |
| 1999-02-20 | FalkirkvHibernianChampionship · Scotland | 1–2 | Championship · Scotland |
| 1999-02-06 | HibernianvStranraerChampionship · Scotland | 2–0 | Championship · Scotland |
| 1999-01-30 | AirdrievHibernianChampionship · Scotland | 1–4 | Championship · Scotland |
| 1999-01-16 | HibernianvHamiltonChampionship · Scotland | 4–0 | Championship · Scotland |
| 1999-01-09 | St MirrenvHibernianChampionship · Scotland | 1–2 | Championship · Scotland |
| 1999-01-02 | HibernianvRaith RvsChampionship · Scotland | 5–1 | Championship · Scotland |
| 1998-12-26 | HibernianvAyrChampionship · Scotland | 3–0 | Championship · Scotland |
| 1998-12-19 | HibernianvClydebankChampionship · Scotland | 3–0 | Championship · Scotland |
| 1998-12-12 | HibernianvFalkirkChampionship · Scotland | 2–1 | Championship · Scotland |
| 1998-12-05 | MortonvHibernianChampionship · Scotland | 1–3 | Championship · Scotland |
| 1998-11-28 | HibernianvAirdrieChampionship · Scotland | 1–0 | Championship · Scotland |
| 1998-11-24 | HibernianvSt MirrenChampionship · Scotland | 4–1 | Championship · Scotland |
| 1998-11-21 | HamiltonvHibernianChampionship · Scotland | 2–2 | Championship · Scotland |
| 1998-11-07 | Raith RvsvHibernianChampionship · Scotland | 1–3 | Championship · Scotland |
| 1998-10-31 | HibernianvClydebankChampionship · Scotland | 2–1 | Championship · Scotland |
| 1998-10-24 | AyrvHibernianChampionship · Scotland | 3–3 | Championship · Scotland |
| 1998-10-17 | HibernianvMortonChampionship · Scotland | 2–1 | Championship · Scotland |
| 1998-10-10 | StranraervHibernianChampionship · Scotland | 0–1 | Championship · Scotland |
| 1998-10-03 | AirdrievHibernianChampionship · Scotland | 1–3 | Championship · Scotland |
| 1998-09-26 | HibernianvHamiltonChampionship · Scotland | 0–0 | Championship · Scotland |
| 1998-09-19 | HibernianvRaith RvsChampionship · Scotland | 3–1 | Championship · Scotland |
| 1998-09-12 | St MirrenvHibernianChampionship · Scotland | 2–0 | Championship · Scotland |
| 1998-09-05 | ClydebankvHibernianChampionship · Scotland | 2–2 | Championship · Scotland |
| 1998-08-29 | HibernianvAyrChampionship · Scotland | 4–2 | Championship · Scotland |
| 1998-08-22 | FalkirkvHibernianChampionship · Scotland | 1–1 | Championship · Scotland |
| 1998-08-15 | HibernianvStranraerChampionship · Scotland | 1–2 | Championship · Scotland |
| 1998-08-04 | MortonvHibernianChampionship · Scotland | 0–1 | Championship · Scotland |
| 1998-05-09 | KilmarnockvHibernianPremiership · Scotland | 1–1 | Premiership · Scotland |
| 1998-05-02 | HibernianvDundee UnitedPremiership · Scotland | 1–2 | Premiership · Scotland |
| 1998-04-25 | CelticvHibernianPremiership · Scotland | 0–0 | Premiership · Scotland |
| 1998-04-18 | DunfermlinevHibernianPremiership · Scotland | 1–1 | Premiership · Scotland |