| 1999-10-02 | YorkvChesterLeague Two · England | 2–2 | League Two · England |
| 1999-09-25 | HullvYorkLeague Two · England | 1–1 | League Two · England |
| 1999-09-18 | ExetervYorkLeague Two · England | 2–1 | League Two · England |
| 1999-09-11 | YorkvPeterboroLeague Two · England | 0–0 | League Two · England |
| 1999-09-04 | RotherhamvYorkLeague Two · England | 1–0 | League Two · England |
| 1999-08-30 | YorkvNorthamptonLeague Two · England | 0–1 | League Two · England |
| 1999-08-28 | BarnetvYorkLeague Two · England | 6–3 | League Two · England |
| 1999-08-21 | YorkvRochdaleLeague Two · England | 0–3 | League Two · England |
| 1999-08-14 | TorquayvYorkLeague Two · England | 0–0 | League Two · England |
| 1999-08-07 | YorkvSwanseaLeague Two · England | 1–0 | League Two · England |
| 1999-05-08 | Man CityvYorkLeague One · England | 4–0 | League One · England |
| 1999-05-01 | YorkvBournemouthLeague One · England | 0–1 | League One · England |
| 1999-04-27 | YorkvBlackpoolLeague One · England | 1–0 | League One · England |
| 1999-04-24 | MacclesfieldvYorkLeague One · England | 1–2 | League One · England |
| 1999-04-17 | YorkvStokeLeague One · England | 2–2 | League One · England |
| 1999-04-13 | NorthamptonvYorkLeague One · England | 2–2 | League One · England |
| 1999-04-10 | YorkvMillwallLeague One · England | 2–1 | League One · England |
| 1999-04-06 | LutonvYorkLeague One · England | 2–1 | League One · England |
| 1999-04-03 | YorkvChesterfieldLeague One · England | 1–2 | League One · England |
| 1999-03-28 | LincolnvYorkLeague One · England | 1–2 | League One · England |
| 1999-03-20 | YorkvWiganLeague One · England | 1–3 | League One · England |
| 1999-03-13 | Notts CountyvYorkLeague One · England | 4–2 | League One · England |
| 1999-03-06 | Bristol RvsvYorkLeague One · England | 2–0 | League One · England |
| 1999-02-27 | YorkvFulhamLeague One · England | 0–3 | League One · England |
| 1999-02-20 | WrexhamvYorkLeague One · England | 1–1 | League One · England |
| 1999-02-13 | YorkvWalsallLeague One · England | 1–2 | League One · England |
| 1999-02-05 | ColchestervYorkLeague One · England | 2–1 | League One · England |
| 1999-01-30 | YorkvOldhamLeague One · England | 0–1 | League One · England |
| 1999-01-23 | YorkvReadingLeague One · England | 1–1 | League One · England |
| 1999-01-16 | GillinghamvYorkLeague One · England | 3–1 | League One · England |
| 1999-01-09 | YorkvPrestonLeague One · England | 0–1 | League One · England |
| 1999-01-02 | WycombevYorkLeague One · England | 1–2 | League One · England |
| 1998-12-28 | OldhamvYorkLeague One · England | 0–2 | League One · England |
| 1998-12-26 | YorkvBurnleyLeague One · England | 3–3 | League One · England |
| 1998-12-19 | YorkvMan CityLeague One · England | 2–1 | League One · England |
| 1998-12-12 | BournemouthvYorkLeague One · England | 2–1 | League One · England |
| 1998-12-08 | YorkvLincolnLeague One · England | 2–1 | League One · England |
| 1998-11-28 | YorkvNorthamptonLeague One · England | 1–1 | League One · England |
| 1998-11-21 | StokevYorkLeague One · England | 2–0 | League One · England |
| 1998-11-10 | YorkvMacclesfieldLeague One · England | 0–2 | League One · England |
| 1998-11-07 | YorkvNotts CountyLeague One · England | 1–1 | League One · England |
| 1998-11-04 | ReadingvYorkLeague One · England | 1–0 | League One · England |
| 1998-10-31 | WiganvYorkLeague One · England | 5–0 | League One · England |
| 1998-10-21 | MillwallvYorkLeague One · England | 3–1 | League One · England |
| 1998-10-17 | ChesterfieldvYorkLeague One · England | 2–1 | League One · England |
| 1998-10-10 | YorkvLutonLeague One · England | 3–3 | League One · England |
| 1998-10-03 | BlackpoolvYorkLeague One · England | 1–2 | League One · England |
| 1998-09-27 | YorkvBristol RvsLeague One · England | 1–0 | League One · England |
| 1998-09-19 | FulhamvYorkLeague One · England | 3–3 | League One · England |
| 1998-09-12 | YorkvWrexhamLeague One · England | 1–1 | League One · England |