| 1999-12-28 | SunderlandvMan UnitedPremier League · England | 2–2 | Premier League · England |
| 1999-12-26 | EvertonvSunderlandPremier League · England | 5–0 | Premier League · England |
| 1999-12-18 | SunderlandvSouthamptonPremier League · England | 2–0 | Premier League · England |
| 1999-12-04 | SunderlandvChelseaPremier League · England | 4–1 | Premier League · England |
| 1999-11-27 | WatfordvSunderlandPremier League · England | 2–3 | Premier League · England |
| 1999-11-20 | SunderlandvLiverpoolPremier League · England | 0–2 | Premier League · England |
| 1999-11-06 | MiddlesbroughvSunderlandPremier League · England | 1–1 | Premier League · England |
| 1999-10-31 | SunderlandvTottenhamPremier League · England | 2–1 | Premier League · England |
| 1999-10-24 | West HamvSunderlandPremier League · England | 1–1 | Premier League · England |
| 1999-10-18 | SunderlandvAston VillaPremier League · England | 2–1 | Premier League · England |
| 1999-10-02 | BradfordvSunderlandPremier League · England | 0–4 | Premier League · England |
| 1999-09-25 | SunderlandvSheffield WedsPremier League · England | 1–0 | Premier League · England |
| 1999-09-18 | DerbyvSunderlandPremier League · England | 0–5 | Premier League · England |
| 1999-09-11 | SunderlandvLeicesterPremier League · England | 2–0 | Premier League · England |
| 1999-08-29 | SunderlandvCoventryPremier League · England | 1–1 | Premier League · England |
| 1999-08-25 | NewcastlevSunderlandPremier League · England | 1–2 | Premier League · England |
| 1999-08-21 | LeedsvSunderlandPremier League · England | 2–1 | Premier League · England |
| 1999-08-14 | SunderlandvArsenalPremier League · England | 0–0 | Premier League · England |
| 1999-08-10 | SunderlandvWatfordPremier League · England | 2–0 | Premier League · England |
| 1999-08-07 | ChelseavSunderlandPremier League · England | 4–0 | Premier League · England |