| 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 |