| 1999-05-16 | NewcastlevBlackburnPremier League · England | 1–1 | Premier League · England |
| 1999-05-16 | Man UnitedvTottenhamPremier League · England | 2–1 | Premier League · England |
| 1999-05-16 | LiverpoolvWimbledonPremier League · England | 3–0 | Premier League · England |
| 1999-05-16 | ChelseavDerbyPremier League · England | 2–1 | Premier League · England |
| 1999-05-16 | SouthamptonvEvertonPremier League · England | 2–0 | Premier League · England |
| 1999-05-12 | BlackburnvMan UnitedPremier League · England | 0–0 | Premier League · England |
| 1999-05-11 | LeedsvArsenalPremier League · England | 1–0 | Premier League · England |
| 1999-05-10 | TottenhamvChelseaPremier League · England | 2–2 | Premier League · England |
| 1999-05-09 | MiddlesbroughvMan UnitedPremier League · England | 0–1 | Premier League · England |
| 1999-05-08 | LeicestervNewcastlePremier League · England | 2–0 | Premier League · England |
| 1999-05-08 | Aston VillavCharltonPremier League · England | 3–4 | Premier League · England |
| 1999-05-08 | EvertonvWest HamPremier League · England | 6–0 | Premier League · England |
| 1999-05-08 | WimbledonvSouthamptonPremier League · England | 0–2 | Premier League · England |
| 1999-05-08 | Sheffield WedsvLiverpoolPremier League · England | 1–0 | Premier League · England |
| 1999-05-08 | BlackburnvNott'm ForestPremier League · England | 1–2 | Premier League · England |
| 1999-05-08 | DerbyvCoventryPremier League · England | 0–0 | Premier League · England |
| 1999-05-05 | ChelseavLeedsPremier League · England | 1–0 | Premier League · England |
| 1999-05-05 | LeicestervDerbyPremier League · England | 1–2 | Premier League · England |
| 1999-05-05 | LiverpoolvMan UnitedPremier League · England | 2–2 | Premier League · England |
| 1999-05-05 | TottenhamvArsenalPremier League · England | 1–3 | Premier League · England |
| 1999-05-02 | ArsenalvDerbyPremier League · England | 1–0 | Premier League · England |
| 1999-05-01 | SouthamptonvLeicesterPremier League · England | 2–1 | Premier League · England |
| 1999-05-01 | NewcastlevMiddlesbroughPremier League · England | 1–1 | Premier League · England |
| 1999-05-01 | ChelseavEvertonPremier League · England | 3–1 | Premier League · England |
| 1999-05-01 | CharltonvBlackburnPremier League · England | 0–0 | Premier League · England |
| 1999-05-01 | Nott'm ForestvSheffield WedsPremier League · England | 2–0 | Premier League · England |
| 1999-05-01 | CoventryvWimbledonPremier League · England | 2–1 | Premier League · England |
| 1999-05-01 | Man UnitedvAston VillaPremier League · England | 2–1 | Premier League · England |
| 1999-05-01 | West HamvLeedsPremier League · England | 1–5 | Premier League · England |
| 1999-05-01 | LiverpoolvTottenhamPremier League · England | 3–2 | Premier League · England |
| 1999-04-25 | Sheffield WedsvChelseaPremier League · England | 0–0 | Premier League · England |
| 1999-04-25 | LeedsvMan UnitedPremier League · England | 1–1 | Premier League · England |
| 1999-04-24 | WimbledonvNewcastlePremier League · England | 1–1 | Premier League · England |
| 1999-04-24 | BlackburnvLiverpoolPremier League · England | 1–3 | Premier League · England |
| 1999-04-24 | LeicestervCoventryPremier League · England | 1–0 | Premier League · England |
| 1999-04-24 | Aston VillavNott'm ForestPremier League · England | 2–0 | Premier League · England |
| 1999-04-24 | TottenhamvWest HamPremier League · England | 1–2 | Premier League · England |
| 1999-04-24 | EvertonvCharltonPremier League · England | 4–1 | Premier League · England |
| 1999-04-24 | MiddlesbroughvArsenalPremier League · England | 1–6 | Premier League · England |
| 1999-04-24 | DerbyvSouthamptonPremier League · England | 0–0 | Premier League · England |
| 1999-04-21 | LiverpoolvLeicesterPremier League · England | 0–1 | Premier League · England |
| 1999-04-21 | Sheffield WedsvNewcastlePremier League · England | 1–1 | Premier League · England |
| 1999-04-20 | CharltonvTottenhamPremier League · England | 1–4 | Premier League · England |
| 1999-04-19 | ArsenalvWimbledonPremier League · England | 5–1 | Premier League · England |
| 1999-04-18 | ChelseavLeicesterPremier League · England | 2–2 | Premier League · England |
| 1999-04-17 | NewcastlevEvertonPremier League · England | 1–3 | Premier League · England |
| 1999-04-17 | Man UnitedvSheffield WedsPremier League · England | 3–0 | Premier League · England |
| 1999-04-17 | West HamvDerbyPremier League · England | 5–1 | Premier League · England |
| 1999-04-17 | Nott'm ForestvTottenhamPremier League · England | 0–1 | Premier League · England |
| 1999-04-17 | CoventryvMiddlesbroughPremier League · England | 1–2 | Premier League · England |