| 1999-10-23 | Sheffield WedsvCoventryPremier League · England | 0–0 | Premier League · England |
| 1999-10-23 | ChelseavArsenalPremier League · England | 2–3 | Premier League · England |
| 1999-10-23 | Aston VillavWimbledonPremier League · England | 1–1 | Premier League · England |
| 1999-10-23 | TottenhamvMan UnitedPremier League · England | 3–1 | Premier League · England |
| 1999-10-18 | SunderlandvAston VillaPremier League · England | 2–1 | Premier League · England |
| 1999-10-17 | MiddlesbroughvWest HamPremier League · England | 2–0 | Premier League · England |
| 1999-10-16 | WimbledonvBradfordPremier League · England | 3–2 | Premier League · England |
| 1999-10-16 | LiverpoolvChelseaPremier League · England | 1–0 | Premier League · England |
| 1999-10-16 | CoventryvNewcastlePremier League · England | 4–1 | Premier League · England |
| 1999-10-16 | LeedsvSheffield WedsPremier League · England | 2–0 | Premier League · England |
| 1999-10-16 | LeicestervSouthamptonPremier League · England | 2–1 | Premier League · England |
| 1999-10-16 | DerbyvTottenhamPremier League · England | 0–1 | Premier League · England |
| 1999-10-16 | ArsenalvEvertonPremier League · England | 4–1 | Premier League · England |
| 1999-10-16 | Man UnitedvWatfordPremier League · England | 4–1 | Premier League · England |
| 1999-10-04 | SouthamptonvDerbyPremier League · England | 3–3 | Premier League · England |
| 1999-10-03 | ChelseavMan UnitedPremier League · England | 5–0 | Premier League · England |
| 1999-10-03 | West HamvArsenalPremier League · England | 2–1 | Premier League · England |
| 1999-10-03 | WatfordvLeedsPremier League · England | 1–2 | Premier League · England |
| 1999-10-03 | NewcastlevMiddlesbroughPremier League · England | 2–1 | Premier League · England |
| 1999-10-03 | TottenhamvLeicesterPremier League · England | 2–3 | Premier League · England |
| 1999-10-02 | BradfordvSunderlandPremier League · England | 0–4 | Premier League · England |
| 1999-10-02 | Aston VillavLiverpoolPremier League · England | 0–0 | Premier League · England |
| 1999-10-02 | Sheffield WedsvWimbledonPremier League · England | 5–1 | Premier League · England |
| 1999-10-02 | EvertonvCoventryPremier League · England | 1–1 | Premier League · England |
| 1999-09-27 | LiverpoolvEvertonPremier League · England | 0–1 | Premier League · England |
| 1999-09-26 | WimbledonvTottenhamPremier League · England | 1–1 | Premier League · England |
| 1999-09-25 | MiddlesbroughvChelseaPremier League · England | 0–1 | Premier League · England |
| 1999-09-25 | Man UnitedvSouthamptonPremier League · England | 3–3 | Premier League · England |
| 1999-09-25 | LeicestervAston VillaPremier League · England | 3–1 | Premier League · England |
| 1999-09-25 | LeedsvNewcastlePremier League · England | 3–2 | Premier League · England |
| 1999-09-25 | SunderlandvSheffield WedsPremier League · England | 1–0 | Premier League · England |
| 1999-09-25 | ArsenalvWatfordPremier League · England | 1–0 | Premier League · England |
| 1999-09-25 | DerbyvBradfordPremier League · England | 0–1 | Premier League · England |
| 1999-09-25 | CoventryvWest HamPremier League · England | 1–0 | Premier League · England |
| 1999-09-19 | TottenhamvCoventryPremier League · England | 3–2 | Premier League · England |
| 1999-09-19 | LeedsvMiddlesbroughPremier League · England | 2–0 | Premier League · England |
| 1999-09-19 | EvertonvWest HamPremier League · England | 1–0 | Premier League · England |
| 1999-09-19 | NewcastlevSheffield WedsPremier League · England | 8–0 | Premier League · England |
| 1999-09-18 | WatfordvChelseaPremier League · England | 1–0 | Premier League · England |
| 1999-09-18 | Aston VillavBradfordPremier League · England | 1–0 | Premier League · England |
| 1999-09-18 | Man UnitedvWimbledonPremier League · England | 1–1 | Premier League · England |
| 1999-09-18 | LeicestervLiverpoolPremier League · England | 2–2 | Premier League · England |
| 1999-09-18 | SouthamptonvArsenalPremier League · England | 0–1 | Premier League · England |
| 1999-09-18 | DerbyvSunderlandPremier League · England | 0–5 | Premier League · England |
| 1999-09-12 | BradfordvTottenhamPremier League · England | 1–1 | Premier League · England |
| 1999-09-11 | ChelseavNewcastlePremier League · England | 1–0 | Premier League · England |
| 1999-09-11 | CoventryvLeedsPremier League · England | 3–4 | Premier League · England |
| 1999-09-11 | LiverpoolvMan UnitedPremier League · England | 2–3 | Premier League · England |
| 1999-09-11 | MiddlesbroughvSouthamptonPremier League · England | 3–2 | Premier League · England |
| 1999-09-11 | ArsenalvAston VillaPremier League · England | 3–1 | Premier League · England |