| 2000-01-29 | SouthendvSwanseaLeague Two · England | 2–1 | League Two · England |
| 2000-01-22 | MansfieldvSouthendLeague Two · England | 3–1 | League Two · England |
| 2000-01-15 | SouthendvRochdaleLeague Two · England | 3–3 | League Two · England |
| 2000-01-08 | BarnetvSouthendLeague Two · England | 2–1 | League Two · England |
| 2000-01-03 | SouthendvRotherhamLeague Two · England | 1–2 | League Two · England |
| 1999-12-28 | TorquayvSouthendLeague Two · England | 0–1 | League Two · England |
| 1999-12-26 | SouthendvNorthamptonLeague Two · England | 2–2 | League Two · England |
| 1999-12-17 | YorkvSouthendLeague Two · England | 2–2 | League Two · England |
| 1999-12-10 | SouthendvBarnetLeague Two · England | 1–3 | League Two · England |
| 1999-12-04 | PlymouthvSouthendLeague Two · England | 3–1 | League Two · England |
| 1999-11-27 | SouthendvDarlingtonLeague Two · England | 1–2 | League Two · England |
| 1999-11-23 | ChestervSouthendLeague Two · England | 0–0 | League Two · England |
| 1999-11-12 | SouthendvHullLeague Two · England | 1–2 | League Two · England |
| 1999-11-06 | ExetervSouthendLeague Two · England | 0–1 | League Two · England |
| 1999-11-02 | SouthendvBrightonLeague Two · England | 2–1 | League Two · England |
| 1999-10-23 | PeterborovSouthendLeague Two · England | 1–0 | League Two · England |
| 1999-10-19 | SouthendvLincolnLeague Two · England | 2–2 | League Two · England |
| 1999-10-16 | SouthendvShrewsburyLeague Two · England | 3–2 | League Two · England |
| 1999-10-09 | CheltenhamvSouthendLeague Two · England | 2–1 | League Two · England |
| 1999-10-02 | CarlislevSouthendLeague Two · England | 1–1 | League Two · England |
| 1999-09-25 | SouthendvPeterboroLeague Two · England | 0–1 | League Two · England |
| 1999-09-18 | SouthendvHalifaxLeague Two · England | 4–1 | League Two · England |
| 1999-09-11 | MacclesfieldvSouthendLeague Two · England | 1–2 | League Two · England |
| 1999-09-04 | HartlepoolvSouthendLeague Two · England | 1–2 | League Two · England |
| 1999-08-30 | SouthendvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1999-08-28 | SwanseavSouthendLeague Two · England | 3–1 | League Two · England |
| 1999-08-21 | SouthendvMansfieldLeague Two · England | 1–0 | League Two · England |
| 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 |