| Date | Match | Score | Competition |
|---|---|---|---|
| 1999-10-23 | YorkHullLeague Two · England | 1–1 | League Two · England |
| 1999-10-19 | HalifaxYorkLeague Two · England | 0–2 | League Two · England |
| 1999-10-16 | BrightonYorkLeague Two · England | 0–1 | League Two · England |
| 1999-10-09 | YorkLeyton OrientLeague Two · England | 2–1 | League Two · England |
| 1999-10-02 | YorkChesterLeague Two · England | 2–2 | League Two · England |
| 1999-09-25 | HullYorkLeague Two · England | 1–1 | League Two · England |
| 1999-09-18 | ExeterYorkLeague Two · England | 2–1 | League Two · England |
| 1999-09-11 | YorkPeterboroLeague Two · England | 0–0 | League Two · England |
| 1999-09-04 | RotherhamYorkLeague Two · England | 1–0 | League Two · England |
| 1999-08-30 | YorkNorthamptonLeague Two · England | 0–1 | League Two · England |
| 1999-08-28 | BarnetYorkLeague Two · England | 6–3 | League Two · England |
| 1999-08-21 | YorkRochdaleLeague Two · England | 0–3 | League Two · England |
| 1999-08-14 | TorquayYorkLeague Two · England | 0–0 | League Two · England |
| 1999-08-07 | YorkSwanseaLeague Two · England | 1–0 | League Two · England |