| 1999-12-28 | WiganvGillinghamLeague One · England | 2–0 | League One · England |
| 1999-12-26 | Notts CountyvWiganLeague One · England | 0–2 | League One · England |
| 1999-12-18 | WiganvBrentfordLeague One · England | 1–0 | League One · England |
| 1999-12-04 | ScunthorpevWiganLeague One · England | 1–2 | League One · England |
| 1999-11-27 | WiganvBurnleyLeague One · England | 1–1 | League One · England |
| 1999-11-23 | BuryvWiganLeague One · England | 2–2 | League One · England |
| 1999-11-16 | WiganvBournemouthLeague One · England | 3–1 | League One · England |
| 1999-11-12 | WiganvWycombeLeague One · England | 2–1 | League One · England |
| 1999-11-06 | BlackpoolvWiganLeague One · England | 2–2 | League One · England |
| 1999-11-02 | WiganvChesterfieldLeague One · England | 3–0 | League One · England |
| 1999-10-26 | ColchestervWiganLeague One · England | 2–2 | League One · England |
| 1999-10-23 | WiganvCardiffLeague One · England | 2–0 | League One · England |
| 1999-10-19 | WrexhamvWiganLeague One · England | 1–1 | League One · England |
| 1999-10-16 | ReadingvWiganLeague One · England | 0–2 | League One · England |
| 1999-10-02 | WiganvLutonLeague One · England | 1–0 | League One · England |
| 1999-09-25 | CardiffvWiganLeague One · England | 0–0 | League One · England |
| 1999-09-18 | StokevWiganLeague One · England | 1–1 | League One · England |
| 1999-09-11 | WiganvBristol RvsLeague One · England | 3–1 | League One · England |
| 1999-08-30 | WiganvCambridgeLeague One · England | 1–1 | League One · England |
| 1999-08-28 | PrestonvWiganLeague One · England | 1–4 | League One · England |
| 1999-08-21 | WiganvBristol CityLeague One · England | 2–1 | League One · England |
| 1999-08-14 | MillwallvWiganLeague One · England | 3–3 | League One · England |
| 1999-08-07 | WiganvScunthorpeLeague One · England | 3–0 | League One · England |
| 1999-05-08 | WiganvChesterfieldLeague One · England | 3–1 | League One · England |
| 1999-05-05 | WycombevWiganLeague One · England | 2–1 | League One · England |
| 1999-05-03 | WiganvBurnleyLeague One · England | 0–0 | League One · England |
| 1999-05-01 | WrexhamvWiganLeague One · England | 0–2 | League One · England |
| 1999-04-29 | NorthamptonvWiganLeague One · England | 3–3 | League One · England |
| 1999-04-27 | WiganvLincolnLeague One · England | 3–1 | League One · England |
| 1999-04-24 | WiganvReadingLeague One · England | 4–1 | League One · England |
| 1999-04-13 | WiganvPrestonLeague One · England | 2–2 | League One · England |
| 1999-04-10 | FulhamvWiganLeague One · England | 2–0 | League One · England |
| 1999-04-05 | WiganvOldhamLeague One · England | 2–0 | League One · England |
| 1999-04-03 | Man CityvWiganLeague One · England | 1–0 | League One · England |
| 1999-03-30 | WiganvBristol RvsLeague One · England | 1–0 | League One · England |
| 1999-03-27 | WiganvStokeLeague One · England | 2–3 | League One · England |
| 1999-03-20 | YorkvWiganLeague One · England | 1–3 | League One · England |
| 1999-03-13 | WiganvGillinghamLeague One · England | 4–1 | League One · England |
| 1999-02-27 | MacclesfieldvWiganLeague One · England | 0–1 | League One · England |
| 1999-02-20 | WiganvBournemouthLeague One · England | 2–1 | League One · England |
| 1999-02-16 | WiganvNotts CountyLeague One · England | 3–0 | League One · England |
| 1999-02-12 | ColchestervWiganLeague One · England | 2–1 | League One · England |
| 1999-01-30 | WalsallvWiganLeague One · England | 1–2 | League One · England |
| 1999-01-23 | LutonvWiganLeague One · England | 0–4 | League One · England |
| 1999-01-09 | MillwallvWiganLeague One · England | 3–1 | League One · England |