| 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 |