| 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 |