| 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 |