| 1998-12-28 | DerbyvMiddlesbroughPremier League · England | 2–1 | Premier League · England |
| 1998-12-26 | MiddlesbroughvLiverpoolPremier League · England | 1–3 | Premier League · England |
| 1998-12-19 | Man UnitedvMiddlesbroughPremier League · England | 2–3 | Premier League · England |
| 1998-12-12 | MiddlesbroughvWest HamPremier League · England | 1–0 | Premier League · England |
| 1998-12-06 | MiddlesbroughvNewcastlePremier League · England | 2–2 | Premier League · England |
| 1998-11-29 | ArsenalvMiddlesbroughPremier League · England | 1–1 | Premier League · England |
| 1998-11-21 | MiddlesbroughvCoventryPremier League · England | 2–0 | Premier League · England |
| 1998-11-14 | CharltonvMiddlesbroughPremier League · England | 1–1 | Premier League · England |
| 1998-11-07 | SouthamptonvMiddlesbroughPremier League · England | 3–3 | Premier League · England |
| 1998-11-01 | MiddlesbroughvNott'm ForestPremier League · England | 1–1 | Premier League · England |
| 1998-10-24 | WimbledonvMiddlesbroughPremier League · England | 2–2 | Premier League · England |
| 1998-10-17 | MiddlesbroughvBlackburnPremier League · England | 2–1 | Premier League · England |
| 1998-10-03 | MiddlesbroughvSheffield WedsPremier League · England | 4–0 | Premier League · England |
| 1998-09-26 | ChelseavMiddlesbroughPremier League · England | 2–0 | Premier League · England |
| 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 |