| 1999-08-14 | RochdalevSouthendLeague Two · England | 2–0 | League Two · England |
| 1999-08-07 | SouthendvPlymouthLeague Two · England | 2–1 | League Two · England |
| 1999-05-08 | SouthendvHartlepoolLeague Two · England | 1–1 | League Two · England |
| 1999-05-01 | BarnetvSouthendLeague Two · England | 0–2 | League Two · England |
| 1999-04-24 | SouthendvBrentfordLeague Two · England | 1–4 | League Two · England |
| 1999-04-17 | PlymouthvSouthendLeague Two · England | 0–3 | League Two · England |
| 1999-04-13 | SouthendvCardiffLeague Two · England | 0–1 | League Two · England |
| 1999-04-10 | MansfieldvSouthendLeague Two · England | 0–0 | League Two · England |
| 1999-04-05 | SouthendvScunthorpeLeague Two · England | 0–1 | League Two · England |
| 1999-04-03 | Leyton OrientvSouthendLeague Two · England | 0–3 | League Two · England |
| 1999-03-30 | RochdalevSouthendLeague Two · England | 1–0 | League Two · England |
| 1999-03-26 | SouthendvHullLeague Two · England | 0–1 | League Two · England |
| 1999-03-20 | DarlingtonvSouthendLeague Two · England | 2–1 | League Two · England |
| 1999-03-13 | SouthendvExeterLeague Two · England | 0–0 | League Two · England |
| 1999-03-06 | SouthendvSwanseaLeague Two · England | 2–0 | League Two · England |
| 1999-02-27 | CambridgevSouthendLeague Two · England | 3–0 | League Two · England |
| 1999-02-20 | SouthendvBrightonLeague Two · England | 3–0 | League Two · England |
| 1999-02-13 | HalifaxvSouthendLeague Two · England | 3–1 | League Two · England |
| 1999-02-06 | RotherhamvSouthendLeague Two · England | 2–2 | League Two · England |
| 1999-01-30 | SouthendvTorquayLeague Two · England | 0–0 | League Two · England |
| 1999-01-23 | SouthendvCarlisleLeague Two · England | 0–1 | League Two · England |
| 1999-01-16 | ShrewsburyvSouthendLeague Two · England | 3–1 | League Two · England |
| 1999-01-09 | SouthendvScarboroughLeague Two · England | 1–0 | League Two · England |
| 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 |