| 1999-12-28 | BournemouthvWrexhamLeague One · England | 1–0 | League One · England |
| 1999-12-26 | WrexhamvPrestonLeague One · England | 0–0 | League One · England |
| 1999-12-18 | ReadingvWrexhamLeague One · England | 2–2 | League One · England |
| 1999-12-04 | WrexhamvBlackpoolLeague One · England | 1–1 | League One · England |
| 1999-11-27 | OldhamvWrexhamLeague One · England | 0–0 | League One · England |
| 1999-11-23 | WrexhamvCambridgeLeague One · England | 1–1 | League One · England |
| 1999-11-12 | MillwallvWrexhamLeague One · England | 0–0 | League One · England |
| 1999-11-06 | WrexhamvBrentfordLeague One · England | 0–1 | League One · England |
| 1999-11-02 | BurnleyvWrexhamLeague One · England | 5–0 | League One · England |
| 1999-10-23 | StokevWrexhamLeague One · England | 2–0 | League One · England |
| 1999-10-19 | WrexhamvWiganLeague One · England | 1–1 | League One · England |
| 1999-10-16 | WrexhamvChesterfieldLeague One · England | 1–1 | League One · England |
| 1999-10-09 | GillinghamvWrexhamLeague One · England | 5–1 | League One · England |
| 1999-10-01 | ColchestervWrexhamLeague One · England | 2–2 | League One · England |
| 1999-09-25 | WrexhamvStokeLeague One · England | 2–3 | League One · England |
| 1999-09-18 | WrexhamvOxfordLeague One · England | 1–0 | League One · England |
| 1999-09-11 | LutonvWrexhamLeague One · England | 3–1 | League One · England |
| 1999-09-03 | WrexhamvNotts CountyLeague One · England | 2–3 | League One · England |
| 1999-08-31 | WycombevWrexhamLeague One · England | 0–1 | League One · England |
| 1999-08-28 | WrexhamvBristol RvsLeague One · England | 2–1 | League One · England |
| 1999-08-22 | CardiffvWrexhamLeague One · England | 1–1 | League One · England |
| 1999-08-14 | WrexhamvBuryLeague One · England | 1–0 | League One · England |
| 1999-08-07 | BlackpoolvWrexhamLeague One · England | 2–1 | League One · England |
| 1999-05-08 | BournemouthvWrexhamLeague One · England | 0–0 | League One · England |
| 1999-05-04 | LincolnvWrexhamLeague One · England | 1–0 | League One · England |
| 1999-05-01 | WrexhamvWiganLeague One · England | 0–2 | League One · England |
| 1999-04-24 | FulhamvWrexhamLeague One · England | 1–1 | League One · England |
| 1999-04-20 | WrexhamvGillinghamLeague One · England | 2–1 | League One · England |
| 1999-04-17 | WrexhamvOldhamLeague One · England | 1–2 | League One · England |
| 1999-04-13 | Notts CountyvWrexhamLeague One · England | 1–1 | League One · England |
| 1999-04-10 | WrexhamvWycombeLeague One · England | 0–2 | League One · England |
| 1999-04-06 | WalsallvWrexhamLeague One · England | 1–0 | League One · England |
| 1999-04-03 | WrexhamvBristol RvsLeague One · England | 1–0 | League One · England |
| 1999-03-27 | MillwallvWrexhamLeague One · England | 3–0 | League One · England |
| 1999-03-20 | WrexhamvBurnleyLeague One · England | 1–1 | League One · England |
| 1999-03-13 | BlackpoolvWrexhamLeague One · England | 1–1 | League One · England |
| 1999-03-06 | WrexhamvChesterfieldLeague One · England | 0–0 | League One · England |
| 1999-03-02 | NorthamptonvWrexhamLeague One · England | 0–2 | League One · England |
| 1999-02-27 | StokevWrexhamLeague One · England | 1–3 | League One · England |
| 1999-02-20 | WrexhamvYorkLeague One · England | 1–1 | League One · England |
| 1999-02-13 | LutonvWrexhamLeague One · England | 1–2 | League One · England |
| 1999-02-06 | MacclesfieldvWrexhamLeague One · England | 0–2 | League One · England |
| 1999-01-30 | WrexhamvPrestonLeague One · England | 0–5 | League One · England |
| 1999-01-15 | ColchestervWrexhamLeague One · England | 1–3 | League One · England |
| 1999-01-09 | ReadingvWrexhamLeague One · England | 4–0 | League One · England |