| 1999-12-28 | YorkvCheltenhamLeague Two · England | 1–2 | League Two · England |
| 1999-12-26 | HartlepoolvYorkLeague Two · England | 2–1 | League Two · England |
| 1999-12-17 | YorkvSouthendLeague Two · England | 2–2 | League Two · England |
| 1999-12-04 | SwanseavYorkLeague Two · England | 1–0 | League Two · England |
| 1999-11-27 | YorkvPlymouthLeague Two · England | 0–0 | League Two · England |
| 1999-11-23 | YorkvShrewsburyLeague Two · England | 1–0 | League Two · England |
| 1999-11-12 | LincolnvYorkLeague Two · England | 4–2 | League Two · England |
| 1999-11-06 | YorkvMacclesfieldLeague Two · England | 0–2 | League Two · England |
| 1999-11-02 | CarlislevYorkLeague Two · England | 0–1 | League Two · England |
| 1999-10-23 | YorkvHullLeague Two · England | 1–1 | League Two · England |
| 1999-10-19 | HalifaxvYorkLeague Two · England | 0–2 | League Two · England |
| 1999-10-16 | BrightonvYorkLeague Two · England | 0–1 | League Two · England |
| 1999-10-09 | YorkvLeyton OrientLeague Two · England | 2–1 | League Two · England |
| 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 |