| 1999-12-28 | ScunthorpevBlackpoolLeague One · England | 1–0 | League One · England |
| 1999-12-26 | OldhamvScunthorpeLeague One · England | 1–1 | League One · England |
| 1999-12-18 | ScunthorpevBuryLeague One · England | 0–2 | League One · England |
| 1999-12-04 | ScunthorpevWiganLeague One · England | 1–2 | League One · England |
| 1999-11-27 | ReadingvScunthorpeLeague One · England | 1–1 | League One · England |
| 1999-11-23 | ScunthorpevGillinghamLeague One · England | 1–4 | League One · England |
| 1999-11-12 | BrentfordvScunthorpeLeague One · England | 4–3 | League One · England |
| 1999-11-06 | ScunthorpevMillwallLeague One · England | 1–4 | League One · England |
| 1999-11-02 | CambridgevScunthorpeLeague One · England | 1–3 | League One · England |
| 1999-10-23 | ChesterfieldvScunthorpeLeague One · England | 1–1 | League One · England |
| 1999-10-19 | ScunthorpevOxfordLeague One · England | 1–0 | League One · England |
| 1999-10-16 | ScunthorpevPrestonLeague One · England | 1–1 | League One · England |
| 1999-10-10 | BurnleyvScunthorpeLeague One · England | 1–2 | League One · England |
| 1999-10-02 | StokevScunthorpeLeague One · England | 1–0 | League One · England |
| 1999-09-25 | ScunthorpevChesterfieldLeague One · England | 0–0 | League One · England |
| 1999-09-18 | ScunthorpevBristol CityLeague One · England | 1–2 | League One · England |
| 1999-09-11 | ColchestervScunthorpeLeague One · England | 0–1 | League One · England |
| 1999-09-04 | ScunthorpevBristol RvsLeague One · England | 0–2 | League One · England |
| 1999-08-30 | CardiffvScunthorpeLeague One · England | 1–1 | League One · England |
| 1999-08-28 | ScunthorpevBournemouthLeague One · England | 3–1 | League One · England |
| 1999-08-21 | Notts CountyvScunthorpeLeague One · England | 3–0 | League One · England |
| 1999-08-14 | ScunthorpevWycombeLeague One · England | 0–1 | League One · England |
| 1999-08-07 | WiganvScunthorpeLeague One · England | 3–0 | League One · England |
| 1999-05-08 | ScunthorpevDarlingtonLeague Two · England | 0–1 | League Two · England |
| 1999-05-01 | CardiffvScunthorpeLeague Two · England | 0–0 | League Two · England |
| 1999-04-27 | HalifaxvScunthorpeLeague Two · England | 1–0 | League Two · England |
| 1999-04-24 | ScunthorpevBarnetLeague Two · England | 3–1 | League Two · England |
| 1999-04-17 | HullvScunthorpeLeague Two · England | 2–3 | League Two · England |
| 1999-04-13 | ScunthorpevPeterboroLeague Two · England | 1–1 | League Two · England |
| 1999-04-10 | ScunthorpevBrentfordLeague Two · England | 0–0 | League Two · England |
| 1999-04-05 | SouthendvScunthorpeLeague Two · England | 0–1 | League Two · England |
| 1999-04-03 | ScunthorpevExeterLeague Two · England | 2–0 | League Two · England |
| 1999-03-30 | PlymouthvScunthorpeLeague Two · England | 5–0 | League Two · England |
| 1999-03-27 | RotherhamvScunthorpeLeague Two · England | 0–0 | League Two · England |
| 1999-03-23 | ScunthorpevSwanseaLeague Two · England | 1–2 | League Two · England |
| 1999-03-20 | ScunthorpevLeyton OrientLeague Two · England | 2–0 | League Two · England |
| 1999-03-13 | ChestervScunthorpeLeague Two · England | 0–2 | League Two · England |
| 1999-03-06 | ScunthorpevBrightonLeague Two · England | 3–1 | League Two · England |
| 1999-02-27 | MansfieldvScunthorpeLeague Two · England | 2–1 | League Two · England |
| 1999-02-20 | ScunthorpevRochdaleLeague Two · England | 0–1 | League Two · England |
| 1999-02-13 | CambridgevScunthorpeLeague Two · England | 0–0 | League Two · England |
| 1999-02-06 | TorquayvScunthorpeLeague Two · England | 1–0 | League Two · England |
| 1999-01-30 | ScunthorpevScarboroughLeague Two · England | 5–1 | League Two · England |
| 1999-01-16 | CarlislevScunthorpeLeague Two · England | 0–1 | League Two · England |
| 1999-01-09 | ScunthorpevShrewsburyLeague Two · England | 3–0 | League Two · England |