| 2000-02-26 | CoventryvTottenhamPremier League · England | 0–1 | Premier League · England |
| 2000-02-12 | LeedsvTottenhamPremier League · England | 1–0 | Premier League · England |
| 2000-02-05 | TottenhamvChelseaPremier League · England | 0–1 | Premier League · England |
| 2000-01-22 | TottenhamvSheffield WedsPremier League · England | 0–1 | Premier League · England |
| 2000-01-15 | EvertonvTottenhamPremier League · England | 2–2 | Premier League · England |
| 2000-01-12 | ChelseavTottenhamPremier League · England | 1–0 | Premier League · England |
| 2000-01-03 | TottenhamvLiverpoolPremier League · England | 1–0 | Premier League · England |
| 1999-12-29 | Aston VillavTottenhamPremier League · England | 1–1 | Premier League · England |
| 1999-12-26 | TottenhamvWatfordPremier League · England | 4–0 | Premier League · England |
| 1999-12-18 | MiddlesbroughvTottenhamPremier League · England | 2–1 | Premier League · England |
| 1999-12-06 | TottenhamvWest HamPremier League · England | 0–0 | Premier League · England |
| 1999-11-28 | NewcastlevTottenhamPremier League · England | 2–1 | Premier League · England |
| 1999-11-20 | SouthamptonvTottenhamPremier League · England | 0–1 | Premier League · England |
| 1999-11-07 | TottenhamvArsenalPremier League · England | 2–1 | Premier League · England |
| 1999-10-31 | SunderlandvTottenhamPremier League · England | 2–1 | Premier League · England |
| 1999-10-23 | TottenhamvMan UnitedPremier League · England | 3–1 | Premier League · England |
| 1999-10-16 | DerbyvTottenhamPremier League · England | 0–1 | Premier League · England |
| 1999-10-03 | TottenhamvLeicesterPremier League · England | 2–3 | Premier League · England |
| 1999-09-26 | WimbledonvTottenhamPremier League · England | 1–1 | Premier League · England |
| 1999-09-19 | TottenhamvCoventryPremier League · England | 3–2 | Premier League · England |
| 1999-09-12 | BradfordvTottenhamPremier League · England | 1–1 | Premier League · England |
| 1999-08-28 | TottenhamvLeedsPremier League · England | 1–2 | Premier League · England |
| 1999-08-21 | Sheffield WedsvTottenhamPremier League · England | 1–2 | Premier League · England |
| 1999-08-14 | TottenhamvEvertonPremier League · England | 3–2 | Premier League · England |
| 1999-08-09 | TottenhamvNewcastlePremier League · England | 3–1 | Premier League · England |
| 1999-08-07 | West HamvTottenhamPremier League · England | 1–0 | Premier League · England |
| 1999-05-16 | Man UnitedvTottenhamPremier League · England | 2–1 | Premier League · England |
| 1999-05-10 | TottenhamvChelseaPremier League · England | 2–2 | Premier League · England |
| 1999-05-05 | TottenhamvArsenalPremier League · England | 1–3 | Premier League · England |
| 1999-05-01 | LiverpoolvTottenhamPremier League · England | 3–2 | Premier League · England |
| 1999-04-24 | TottenhamvWest HamPremier League · England | 1–2 | Premier League · England |
| 1999-04-20 | CharltonvTottenhamPremier League · England | 1–4 | Premier League · England |
| 1999-04-17 | Nott'm ForestvTottenhamPremier League · England | 0–1 | Premier League · England |
| 1999-04-05 | NewcastlevTottenhamPremier League · England | 1–1 | Premier League · England |
| 1999-04-03 | TottenhamvLeicesterPremier League · England | 0–2 | Premier League · England |
| 1999-03-13 | TottenhamvAston VillaPremier League · England | 1–0 | Premier League · England |
| 1999-03-10 | LeedsvTottenhamPremier League · England | 2–0 | Premier League · England |
| 1999-03-02 | TottenhamvSouthamptonPremier League · England | 3–0 | Premier League · England |
| 1999-02-27 | TottenhamvDerbyPremier League · England | 1–1 | Premier League · England |
| 1999-02-20 | MiddlesbroughvTottenhamPremier League · England | 0–0 | Premier League · England |
| 1999-02-06 | TottenhamvCoventryPremier League · England | 0–0 | Premier League · England |
| 1999-01-30 | BlackburnvTottenhamPremier League · England | 1–1 | Premier League · England |
| 1999-01-16 | TottenhamvWimbledonPremier League · England | 0–0 | Premier League · England |
| 1999-01-09 | Sheffield WedsvTottenhamPremier League · England | 0–0 | Premier League · England |
| 1998-12-28 | TottenhamvEvertonPremier League · England | 4–1 | Premier League · England |
| 1998-12-26 | CoventryvTottenhamPremier League · England | 1–1 | Premier League · England |
| 1998-12-19 | ChelseavTottenhamPremier League · England | 2–0 | Premier League · England |
| 1998-12-12 | TottenhamvMan UnitedPremier League · England | 2–2 | Premier League · England |
| 1998-12-05 | TottenhamvLiverpoolPremier League · England | 2–1 | Premier League · England |
| 1998-11-28 | West HamvTottenhamPremier League · England | 2–1 | Premier League · England |