| 1999-11-23 | LutonvPrestonLeague One · England | 0–2 | League One · England |
| 1999-11-12 | CambridgevLutonLeague One · England | 3–1 | League One · England |
| 1999-11-06 | LutonvBurnleyLeague One · England | 2–1 | League One · England |
| 1999-11-02 | MillwallvLutonLeague One · England | 1–0 | League One · England |
| 1999-10-23 | OxfordvLutonLeague One · England | 0–1 | League One · England |
| 1999-10-19 | LutonvWycombeLeague One · England | 1–1 | League One · England |
| 1999-10-16 | LutonvGillinghamLeague One · England | 3–1 | League One · England |
| 1999-10-09 | OldhamvLutonLeague One · England | 2–1 | League One · England |
| 1999-10-02 | WiganvLutonLeague One · England | 1–0 | League One · England |
| 1999-09-25 | LutonvOxfordLeague One · England | 4–2 | League One · England |
| 1999-09-18 | BrentfordvLutonLeague One · England | 2–0 | League One · England |
| 1999-09-11 | LutonvWrexhamLeague One · England | 3–1 | League One · England |
| 1999-09-04 | LutonvBuryLeague One · England | 1–1 | League One · England |
| 1999-08-31 | BournemouthvLutonLeague One · England | 1–0 | League One · England |
| 1999-08-28 | LutonvCardiffLeague One · England | 1–0 | League One · England |
| 1999-08-21 | ReadingvLutonLeague One · England | 1–2 | League One · England |
| 1999-08-14 | LutonvBlackpoolLeague One · England | 3–2 | League One · England |
| 1999-08-07 | Notts CountyvLutonLeague One · England | 0–0 | League One · England |
| 1999-05-08 | MillwallvLutonLeague One · England | 0–1 | League One · England |
| 1999-05-01 | LutonvMacclesfieldLeague One · England | 1–2 | League One · England |
| 1999-04-27 | LutonvChesterfieldLeague One · England | 1–0 | League One · England |
| 1999-04-24 | Notts CountyvLutonLeague One · England | 1–2 | League One · England |
| 1999-04-17 | LutonvLincolnLeague One · England | 0–1 | League One · England |
| 1999-04-14 | Man CityvLutonLeague One · England | 2–0 | League One · England |
| 1999-04-10 | NorthamptonvLutonLeague One · England | 1–0 | League One · England |
| 1999-04-06 | LutonvYorkLeague One · England | 2–1 | League One · England |
| 1999-04-02 | OldhamvLutonLeague One · England | 1–1 | League One · England |
| 1999-03-27 | LutonvGillinghamLeague One · England | 1–0 | League One · England |
| 1999-03-23 | LutonvReadingLeague One · England | 1–1 | League One · England |
| 1999-03-20 | ChesterfieldvLutonLeague One · England | 3–1 | League One · England |
| 1999-03-13 | LutonvStokeLeague One · England | 1–2 | League One · England |
| 1999-03-09 | LutonvFulhamLeague One · England | 0–4 | League One · England |
| 1999-03-06 | WalsallvLutonLeague One · England | 1–0 | League One · England |
| 1999-02-27 | LutonvBlackpoolLeague One · England | 1–0 | League One · England |
| 1999-02-23 | LutonvNotts CountyLeague One · England | 0–1 | League One · England |
| 1999-02-20 | Bristol RvsvLutonLeague One · England | 1–0 | League One · England |
| 1999-02-13 | LutonvWrexhamLeague One · England | 1–2 | League One · England |
| 1999-02-06 | BurnleyvLutonLeague One · England | 1–2 | League One · England |
| 1999-01-30 | LutonvBournemouthLeague One · England | 2–2 | League One · England |
| 1999-01-23 | LutonvWiganLeague One · England | 0–4 | League One · England |
| 1999-01-16 | PrestonvLutonLeague One · England | 2–1 | League One · England |
| 1999-01-09 | LutonvWycombeLeague One · England | 3–1 | League One · England |
| 1999-01-02 | ColchestervLutonLeague One · England | 2–2 | League One · England |
| 1998-12-28 | BournemouthvLutonLeague One · England | 1–0 | League One · England |
| 1998-12-19 | LutonvMillwallLeague One · England | 1–2 | League One · England |
| 1998-12-12 | MacclesfieldvLutonLeague One · England | 2–2 | League One · England |
| 1998-11-28 | LutonvMan CityLeague One · England | 1–1 | League One · England |
| 1998-11-21 | LincolnvLutonLeague One · England | 2–2 | League One · England |
| 1998-11-07 | StokevLutonLeague One · England | 3–1 | League One · England |
| 1998-10-24 | GillinghamvLutonLeague One · England | 1–0 | League One · England |