| 1998-09-19 | MiddlesbroughvEvertonPremier League · England | 2–2 | Premier League · England |
| 1998-09-13 | TottenhamvMiddlesbroughPremier League · England | 0–3 | Premier League · England |
| 1998-09-09 | LeicestervMiddlesbroughPremier League · England | 0–1 | Premier League · England |
| 1998-08-29 | MiddlesbroughvDerbyPremier League · England | 1–1 | Premier League · England |
| 1998-08-23 | Aston VillavMiddlesbroughPremier League · England | 3–1 | Premier League · England |
| 1998-08-15 | MiddlesbroughvLeedsPremier League · England | 0–0 | Premier League · England |
| 1997-05-11 | LeedsvMiddlesbroughPremier League · England | 1–1 | Premier League · England |
| 1997-05-08 | BlackburnvMiddlesbroughPremier League · England | 0–0 | Premier League · England |
| 1997-05-05 | Man UnitedvMiddlesbroughPremier League · England | 3–3 | Premier League · England |
| 1997-05-03 | MiddlesbroughvAston VillaPremier League · England | 3–2 | Premier League · England |
| 1997-04-24 | TottenhamvMiddlesbroughPremier League · England | 1–0 | Premier League · England |
| 1997-04-19 | MiddlesbroughvSunderlandPremier League · England | 0–1 | Premier League · England |
| 1997-04-09 | West HamvMiddlesbroughPremier League · England | 0–0 | Premier League · England |
| 1997-03-24 | MiddlesbroughvNott'm ForestPremier League · England | 1–1 | Premier League · England |
| 1997-03-22 | MiddlesbroughvChelseaPremier League · England | 1–0 | Premier League · England |
| 1997-03-19 | MiddlesbroughvBlackburnPremier League · England | 2–1 | Premier League · England |
| 1997-03-15 | LeicestervMiddlesbroughPremier League · England | 1–3 | Premier League · England |
| 1997-03-05 | MiddlesbroughvDerbyPremier League · England | 6–1 | Premier League · England |
| 1997-03-01 | Sheffield WedsvMiddlesbroughPremier League · England | 3–1 | Premier League · England |
| 1997-02-22 | MiddlesbroughvNewcastlePremier League · England | 0–1 | Premier League · England |
| 1997-02-01 | WimbledonvMiddlesbroughPremier League · England | 1–1 | Premier League · England |
| 1997-01-18 | MiddlesbroughvSheffield WedsPremier League · England | 4–2 | Premier League · England |
| 1997-01-11 | MiddlesbroughvSouthamptonPremier League · England | 0–1 | Premier League · England |
| 1997-01-01 | ArsenalvMiddlesbroughPremier League · England | 2–0 | Premier League · England |
| 1996-12-28 | CoventryvMiddlesbroughPremier League · England | 3–0 | Premier League · England |
| 1996-12-26 | MiddlesbroughvEvertonPremier League · England | 4–2 | Premier League · England |
| 1996-12-14 | LiverpoolvMiddlesbroughPremier League · England | 5–1 | Premier League · England |
| 1996-12-07 | MiddlesbroughvLeedsPremier League · England | 0–0 | Premier League · England |
| 1996-12-03 | MiddlesbroughvLeicesterPremier League · England | 0–2 | Premier League · England |
| 1996-11-30 | Aston VillavMiddlesbroughPremier League · England | 1–0 | Premier League · England |
| 1996-11-23 | MiddlesbroughvMan UnitedPremier League · England | 2–2 | Premier League · England |
| 1996-11-17 | DerbyvMiddlesbroughPremier League · England | 2–1 | Premier League · England |
| 1996-11-03 | NewcastlevMiddlesbroughPremier League · England | 3–1 | Premier League · England |
| 1996-10-26 | MiddlesbroughvWimbledonPremier League · England | 0–0 | Premier League · England |
| 1996-10-19 | MiddlesbroughvTottenhamPremier League · England | 0–3 | Premier League · England |
| 1996-10-14 | SunderlandvMiddlesbroughPremier League · England | 2–2 | Premier League · England |
| 1996-09-28 | SouthamptonvMiddlesbroughPremier League · England | 4–0 | Premier League · England |
| 1996-09-21 | MiddlesbroughvArsenalPremier League · England | 0–2 | Premier League · England |
| 1996-09-14 | EvertonvMiddlesbroughPremier League · England | 1–2 | Premier League · England |
| 1996-09-07 | MiddlesbroughvCoventryPremier League · England | 4–0 | Premier League · England |
| 1996-09-04 | MiddlesbroughvWest HamPremier League · England | 4–1 | Premier League · England |
| 1996-08-24 | Nott'm ForestvMiddlesbroughPremier League · England | 1–1 | Premier League · England |
| 1996-08-21 | ChelseavMiddlesbroughPremier League · England | 1–0 | Premier League · England |
| 1996-08-17 | MiddlesbroughvLiverpoolPremier League · England | 3–3 | Premier League · England |
| 1996-05-04 | MiddlesbroughvMan UnitedPremier League · England | 0–3 | Premier League · England |
| 1996-04-27 | LiverpoolvMiddlesbroughPremier League · England | 1–0 | Premier League · England |
| 1996-04-13 | MiddlesbroughvWimbledonPremier League · England | 1–2 | Premier League · England |
| 1996-04-08 | TottenhamvMiddlesbroughPremier League · England | 1–1 | Premier League · England |
| 1996-04-05 | MiddlesbroughvSheffield WedsPremier League · England | 3–1 | Premier League · England |
| 1996-03-30 | LeedsvMiddlesbroughPremier League · England | 0–1 | Premier League · England |