| 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 |
| 1998-12-28 | SunderlandvCreweChampionship · England | 2–0 | Championship · England |
| 1998-12-26 | TranmerevSunderlandChampionship · England | 1–0 | Championship · England |
| 1998-12-19 | BirminghamvSunderlandChampionship · England | 0–0 | Championship · England |
| 1998-12-15 | SunderlandvCrystal PalaceChampionship · England | 2–0 | Championship · England |
| 1998-12-12 | SunderlandvPort ValeChampionship · England | 2–0 | Championship · England |
| 1998-12-05 | SunderlandvStockportChampionship · England | 1–0 | Championship · England |
| 1998-11-28 | Sheffield UnitedvSunderlandChampionship · England | 0–4 | Championship · England |
| 1998-11-21 | SunderlandvBarnsleyChampionship · England | 2–3 | Championship · England |
| 1998-11-14 | Port ValevSunderlandChampionship · England | 0–2 | Championship · England |
| 1998-11-07 | SunderlandvGrimsbyChampionship · England | 3–1 | Championship · England |
| 1998-11-03 | CrewevSunderlandChampionship · England | 1–4 | Championship · England |
| 1998-11-01 | BoltonvSunderlandChampionship · England | 0–3 | Championship · England |
| 1998-10-24 | SunderlandvBuryChampionship · England | 1–0 | Championship · England |
| 1998-10-21 | HuddersfieldvSunderlandChampionship · England | 1–1 | Championship · England |
| 1998-10-18 | West BromvSunderlandChampionship · England | 2–3 | Championship · England |
| 1998-10-03 | SunderlandvBradfordChampionship · England | 0–0 | Championship · England |
| 1998-09-29 | NorwichvSunderlandChampionship · England | 2–2 | Championship · England |
| 1998-09-26 | PortsmouthvSunderlandChampionship · England | 1–1 | Championship · England |
| 1998-09-19 | SunderlandvOxfordChampionship · England | 7–0 | Championship · England |
| 1998-09-12 | WolvesvSunderlandChampionship · England | 1–1 | Championship · England |
| 1998-09-08 | SunderlandvBristol CityChampionship · England | 1–1 | Championship · England |
| 1998-08-29 | IpswichvSunderlandChampionship · England | 0–2 | Championship · England |
| 1998-08-25 | SunderlandvWatfordChampionship · England | 4–1 | Championship · England |
| 1998-08-22 | SunderlandvTranmereChampionship · England | 5–0 | Championship · England |
| 1998-08-15 | SwindonvSunderlandChampionship · England | 1–1 | Championship · England |
| 1998-08-08 | SunderlandvQPRChampionship · England | 1–0 | Championship · England |