| 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 |