| 1999-12-28 | Bristol CityvLutonLeague One · England | 0–0 | League One · England |
| 1999-12-26 | BrentfordvBristol CityLeague One · England | 2–1 | League One · England |
| 1999-12-17 | Bristol CityvWycombeLeague One · England | 0–0 | League One · England |
| 1999-12-07 | ChesterfieldvBristol CityLeague One · England | 0–2 | League One · England |
| 1999-12-04 | Bristol CityvReadingLeague One · England | 3–1 | League One · England |
| 1999-11-27 | Notts CountyvBristol CityLeague One · England | 4–4 | League One · England |
| 1999-11-23 | Bristol CityvOldhamLeague One · England | 1–1 | League One · England |
| 1999-11-14 | StokevBristol CityLeague One · England | 1–1 | League One · England |
| 1999-11-06 | Bristol CityvCambridgeLeague One · England | 1–1 | League One · England |
| 1999-11-02 | GillinghamvBristol CityLeague One · England | 3–0 | League One · England |
| 1999-10-23 | BurnleyvBristol CityLeague One · England | 2–0 | League One · England |
| 1999-10-19 | Bristol CityvColchesterLeague One · England | 1–1 | League One · England |
| 1999-10-17 | Bristol CityvBristol RvsLeague One · England | 0–0 | League One · England |
| 1999-10-09 | PrestonvBristol CityLeague One · England | 1–0 | League One · England |
| 1999-10-02 | OxfordvBristol CityLeague One · England | 3–0 | League One · England |
| 1999-09-25 | Bristol CityvBurnleyLeague One · England | 0–0 | League One · England |
| 1999-09-18 | ScunthorpevBristol CityLeague One · England | 1–2 | League One · England |
| 1999-09-11 | Bristol CityvMillwallLeague One · England | 0–0 | League One · England |
| 1999-09-04 | Bristol CityvBlackpoolLeague One · England | 5–2 | League One · England |
| 1999-08-28 | Bristol CityvBuryLeague One · England | 1–1 | League One · England |
| 1999-08-21 | WiganvBristol CityLeague One · England | 2–1 | League One · England |
| 1999-08-14 | Bristol CityvBournemouthLeague One · England | 3–1 | League One · England |
| 1999-08-07 | ReadingvBristol CityLeague One · England | 2–1 | League One · England |
| 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 |