| 1998-12-28 | TorquayvSouthendLeague Two · England | 2–0 | League Two · England |
| 1998-12-26 | SouthendvPeterboroLeague Two · England | 2–0 | League Two · England |
| 1998-12-19 | HartlepoolvSouthendLeague Two · England | 2–4 | League Two · England |
| 1998-12-12 | SouthendvBarnetLeague Two · England | 2–3 | League Two · England |
| 1998-11-28 | CardiffvSouthendLeague Two · England | 2–0 | League Two · England |
| 1998-11-21 | SouthendvPlymouthLeague Two · England | 1–0 | League Two · England |
| 1998-11-10 | BrentfordvSouthendLeague Two · England | 4–1 | League Two · England |
| 1998-11-07 | ExetervSouthendLeague Two · England | 2–1 | League Two · England |
| 1998-10-31 | SouthendvDarlingtonLeague Two · England | 2–1 | League Two · England |
| 1998-10-24 | HullvSouthendLeague Two · England | 1–1 | League Two · England |
| 1998-10-20 | SouthendvMansfieldLeague Two · England | 1–2 | League Two · England |
| 1998-10-17 | SouthendvLeyton OrientLeague Two · England | 2–2 | League Two · England |
| 1998-10-10 | ScunthorpevSouthendLeague Two · England | 1–1 | League Two · England |
| 1998-10-03 | SouthendvRochdaleLeague Two · England | 1–1 | League Two · England |
| 1998-09-27 | SwanseavSouthendLeague Two · England | 3–1 | League Two · England |
| 1998-09-19 | SouthendvCambridgeLeague Two · England | 0–1 | League Two · England |
| 1998-09-12 | BrightonvSouthendLeague Two · England | 0–2 | League Two · England |
| 1998-09-08 | SouthendvHalifaxLeague Two · England | 0–0 | League Two · England |
| 1998-09-05 | SouthendvRotherhamLeague Two · England | 3–0 | League Two · England |
| 1998-09-01 | CarlislevSouthendLeague Two · England | 3–0 | League Two · England |
| 1998-08-29 | SouthendvChesterLeague Two · England | 0–1 | League Two · England |
| 1998-08-22 | PeterborovSouthendLeague Two · England | 1–1 | League Two · England |
| 1998-08-15 | SouthendvShrewsburyLeague Two · England | 2–1 | League Two · England |
| 1998-08-08 | ScarboroughvSouthendLeague Two · England | 1–2 | League Two · England |