| 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 |
| 1999-05-09 | SunderlandvBirminghamChampionship · England | 2–1 | Championship · England |
| 1999-05-01 | StockportvSunderlandChampionship · England | 0–1 | Championship · England |
| 1999-04-24 | SunderlandvSheffield UnitedChampionship · England | 0–0 | Championship · England |
| 1999-04-16 | BarnsleyvSunderlandChampionship · England | 1–3 | Championship · England |
| 1999-04-13 | BuryvSunderlandChampionship · England | 2–5 | Championship · England |
| 1999-04-10 | SunderlandvHuddersfieldChampionship · England | 2–0 | Championship · England |
| 1999-04-05 | Crystal PalacevSunderlandChampionship · England | 1–1 | Championship · England |
| 1999-04-03 | SunderlandvWest BromChampionship · England | 3–0 | Championship · England |
| 1999-03-20 | SunderlandvBoltonChampionship · England | 3–1 | Championship · England |
| 1999-03-13 | GrimsbyvSunderlandChampionship · England | 0–2 | Championship · England |
| 1999-03-09 | BradfordvSunderlandChampionship · England | 0–1 | Championship · England |
| 1999-03-06 | SunderlandvNorwichChampionship · England | 1–0 | Championship · England |
| 1999-03-02 | SunderlandvPortsmouthChampionship · England | 2–0 | Championship · England |
| 1999-02-27 | OxfordvSunderlandChampionship · England | 0–0 | Championship · England |
| 1999-02-20 | SunderlandvWolvesChampionship · England | 2–1 | Championship · England |
| 1999-02-13 | Bristol CityvSunderlandChampionship · England | 0–1 | Championship · England |
| 1999-02-06 | SunderlandvSwindonChampionship · England | 2–0 | Championship · England |
| 1999-01-30 | WatfordvSunderlandChampionship · England | 2–1 | Championship · England |
| 1999-01-17 | SunderlandvIpswichChampionship · England | 2–1 | Championship · England |
| 1999-01-09 | QPRvSunderlandChampionship · England | 2–2 | Championship · England |