| 1999-01-02 | ChestervSouthendLeague Two · England | 1–1 | League Two · England |
| 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 |
| 1998-05-02 | SouthendvWrexhamLeague One · England | 1–3 | League One · England |
| 1998-04-25 | OldhamvSouthendLeague One · England | 2–0 | League One · England |
| 1998-04-18 | YorkvSouthendLeague One · England | 1–1 | League One · England |
| 1998-04-13 | SouthendvGillinghamLeague One · England | 0–0 | League One · England |
| 1998-04-11 | PrestonvSouthendLeague One · England | 1–0 | League One · England |
| 1998-04-03 | SouthendvChesterfieldLeague One · England | 0–2 | League One · England |
| 1998-03-27 | Bristol RvsvSouthendLeague One · England | 2–0 | League One · England |
| 1998-03-21 | SouthendvBournemouthLeague One · England | 5–3 | League One · England |
| 1998-03-17 | WiganvSouthendLeague One · England | 1–3 | League One · England |
| 1998-03-14 | WatfordvSouthendLeague One · England | 1–1 | League One · England |
| 1998-03-07 | SouthendvGrimsbyLeague One · England | 0–1 | League One · England |
| 1998-02-28 | Bristol CityvSouthendLeague One · England | 1–0 | League One · England |
| 1998-02-24 | SouthendvPlymouthLeague One · England | 3–0 | League One · England |
| 1998-02-21 | SouthendvBlackpoolLeague One · England | 2–1 | League One · England |
| 1998-02-14 | NorthamptonvSouthendLeague One · England | 3–1 | League One · England |
| 1998-02-07 | FulhamvSouthendLeague One · England | 2–0 | League One · England |
| 1998-01-31 | SouthendvMillwallLeague One · England | 0–0 | League One · England |
| 1998-01-24 | BurnleyvSouthendLeague One · England | 1–0 | League One · England |
| 1998-01-17 | SouthendvWalsallLeague One · England | 0–1 | League One · England |
| 1998-01-10 | CarlislevSouthendLeague One · England | 5–0 | League One · England |
| 1998-01-03 | SouthendvLutonLeague One · England | 1–2 | League One · England |
| 1997-12-28 | SouthendvWycombeLeague One · England | 1–2 | League One · England |
| 1997-12-26 | BrentfordvSouthendLeague One · England | 1–1 | League One · England |
| 1997-12-19 | SouthendvYorkLeague One · England | 4–4 | League One · England |
| 1997-12-13 | GillinghamvSouthendLeague One · England | 1–2 | League One · England |