| 1999-04-17 | LiverpoolvAston VillaPremier League · England | 0–1 | Premier League · England |
| 1999-04-17 | SouthamptonvBlackburnPremier League · England | 3–3 | Premier League · England |
| 1999-04-17 | CharltonvLeedsPremier League · England | 1–1 | Premier League · England |
| 1999-04-14 | MiddlesbroughvChelseaPremier League · England | 0–0 | Premier League · England |
| 1999-04-12 | LeedsvLiverpoolPremier League · England | 0–0 | Premier League · England |
| 1999-04-11 | EvertonvCoventryPremier League · England | 2–0 | Premier League · England |
| 1999-04-11 | WimbledonvChelseaPremier League · England | 1–2 | Premier League · England |
| 1999-04-10 | DerbyvNott'm ForestPremier League · England | 1–0 | Premier League · England |
| 1999-04-10 | Aston VillavSouthamptonPremier League · England | 3–0 | Premier League · England |
| 1999-04-10 | MiddlesbroughvCharltonPremier League · England | 2–0 | Premier League · England |
| 1999-04-10 | LeicestervWest HamPremier League · England | 0–0 | Premier League · England |
| 1999-04-06 | LeicestervAston VillaPremier League · England | 2–2 | Premier League · England |
| 1999-04-06 | ArsenalvBlackburnPremier League · England | 1–0 | Premier League · England |
| 1999-04-05 | West HamvCharltonPremier League · England | 0–1 | Premier League · England |
| 1999-04-05 | EvertonvSheffield WedsPremier League · England | 1–2 | Premier League · England |
| 1999-04-05 | NewcastlevTottenhamPremier League · England | 1–1 | Premier League · England |
| 1999-04-05 | CoventryvSouthamptonPremier League · England | 1–0 | Premier League · England |
| 1999-04-05 | Nott'm ForestvLiverpoolPremier League · England | 2–2 | Premier League · England |
| 1999-04-05 | MiddlesbroughvWimbledonPremier League · England | 3–1 | Premier League · England |
| 1999-04-03 | LiverpoolvEvertonPremier League · England | 3–2 | Premier League · England |
| 1999-04-03 | WimbledonvMan UnitedPremier League · England | 1–1 | Premier League · England |
| 1999-04-03 | TottenhamvLeicesterPremier League · England | 0–2 | Premier League · England |
| 1999-04-03 | BlackburnvMiddlesbroughPremier League · England | 0–0 | Premier League · England |
| 1999-04-03 | CharltonvChelseaPremier League · England | 0–1 | Premier League · England |
| 1999-04-03 | LeedsvNott'm ForestPremier League · England | 3–1 | Premier League · England |
| 1999-04-03 | Sheffield WedsvCoventryPremier League · England | 1–2 | Premier League · England |
| 1999-04-03 | SouthamptonvArsenalPremier League · England | 0–0 | Premier League · England |
| 1999-04-03 | DerbyvNewcastlePremier League · England | 3–4 | Premier League · England |
| 1999-04-02 | Aston VillavWest HamPremier League · England | 0–0 | Premier League · England |
| 1999-03-21 | Man UnitedvEvertonPremier League · England | 3–1 | Premier League · England |
| 1999-03-21 | Aston VillavChelseaPremier League · England | 0–3 | Premier League · England |
| 1999-03-20 | West HamvNewcastlePremier League · England | 2–0 | Premier League · England |
| 1999-03-20 | ArsenalvCoventryPremier League · England | 2–0 | Premier League · England |
| 1999-03-20 | LeedsvDerbyPremier League · England | 4–1 | Premier League · England |
| 1999-03-20 | SouthamptonvSheffield WedsPremier League · England | 1–0 | Premier League · England |
| 1999-03-20 | BlackburnvWimbledonPremier League · England | 3–1 | Premier League · England |
| 1999-03-20 | Nott'm ForestvMiddlesbroughPremier League · England | 1–2 | Premier League · England |
| 1999-03-14 | MiddlesbroughvSouthamptonPremier League · England | 3–0 | Premier League · England |
| 1999-03-13 | LeicestervCharltonPremier League · England | 1–1 | Premier League · England |
| 1999-03-13 | NewcastlevMan UnitedPremier League · England | 1–2 | Premier League · England |
| 1999-03-13 | WimbledonvNott'm ForestPremier League · England | 1–3 | Premier League · England |
| 1999-03-13 | Sheffield WedsvLeedsPremier League · England | 0–2 | Premier League · England |
| 1999-03-13 | ChelseavWest HamPremier League · England | 0–1 | Premier League · England |
| 1999-03-13 | CoventryvBlackburnPremier League · England | 1–1 | Premier League · England |
| 1999-03-13 | TottenhamvAston VillaPremier League · England | 1–0 | Premier League · England |
| 1999-03-13 | DerbyvLiverpoolPremier League · England | 3–2 | Premier League · England |
| 1999-03-13 | EvertonvArsenalPremier League · England | 0–2 | Premier League · England |
| 1999-03-10 | BlackburnvEvertonPremier League · England | 1–2 | Premier League · England |
| 1999-03-10 | DerbyvAston VillaPremier League · England | 2–1 | Premier League · England |
| 1999-03-10 | LeedsvTottenhamPremier League · England | 2–0 | Premier League · England |