| 1999-05-09 | Bristol CityvNorwichChampionship · England | 1–0 | Championship · England |
| 1999-05-01 | Sheffield UnitedvBristol CityChampionship · England | 3–1 | Championship · England |
| 1999-04-27 | CrewevBristol CityChampionship · England | 1–0 | Championship · England |
| 1999-04-24 | Bristol CityvBirminghamChampionship · England | 1–2 | Championship · England |
| 1999-04-17 | StockportvBristol CityChampionship · England | 2–2 | Championship · England |
| 1999-04-13 | BoltonvBristol CityChampionship · England | 1–0 | Championship · England |
| 1999-04-10 | Bristol CityvGrimsbyChampionship · England | 4–1 | Championship · England |
| 1999-04-05 | PortsmouthvBristol CityChampionship · England | 0–1 | Championship · England |
| 1999-04-03 | Bristol CityvPort ValeChampionship · England | 2–0 | Championship · England |
| 1999-03-23 | BarnsleyvBristol CityChampionship · England | 2–0 | Championship · England |
| 1999-03-20 | Bristol CityvBradfordChampionship · England | 2–3 | Championship · England |
| 1999-03-13 | WolvesvBristol CityChampionship · England | 3–0 | Championship · England |
| 1999-03-09 | Bristol CityvBuryChampionship · England | 1–1 | Championship · England |
| 1999-02-27 | Bristol CityvIpswichChampionship · England | 0–1 | Championship · England |
| 1999-02-20 | West BromvBristol CityChampionship · England | 2–2 | Championship · England |
| 1999-02-13 | Bristol CityvSunderlandChampionship · England | 0–1 | Championship · England |
| 1999-02-05 | Bristol CityvQPRChampionship · England | 0–0 | Championship · England |
| 1999-01-30 | HuddersfieldvBristol CityChampionship · England | 2–2 | Championship · England |
| 1999-01-16 | Bristol CityvTranmereChampionship · England | 1–1 | Championship · England |
| 1999-01-09 | OxfordvBristol CityChampionship · England | 0–0 | Championship · England |