| 2008-12-28 | Milton Keynes DonsvSouthendLeague One · England | 2–0 | League One · England |
| 2008-12-26 | SouthendvNorthamptonLeague One · England | 1–0 | League One · England |
| 2008-12-19 | HartlepoolvSouthendLeague One · England | 3–0 | League One · England |
| 2008-12-13 | SouthendvHuddersfieldLeague One · England | 0–1 | League One · England |
| 2008-12-06 | LeicestervSouthendLeague One · England | 3–0 | League One · England |
| 2008-11-25 | CheltenhamvSouthendLeague One · England | 0–0 | League One · England |
| 2008-11-22 | SouthendvOldhamLeague One · England | 1–2 | League One · England |
| 2008-11-15 | TranmerevSouthendLeague One · England | 2–2 | League One · England |
| 2008-11-01 | SouthendvColchesterLeague One · England | 3–3 | League One · England |
| 2008-10-28 | SouthendvLeedsLeague One · England | 1–0 | League One · England |
| 2008-10-25 | Bristol RvsvSouthendLeague One · England | 4–2 | League One · England |
| 2008-10-21 | ScunthorpevSouthendLeague One · England | 1–1 | League One · England |
| 2008-10-18 | SouthendvSwindonLeague One · England | 2–1 | League One · England |
| 2008-10-11 | SouthendvStockportLeague One · England | 1–1 | League One · England |
| 2008-10-04 | YeovilvSouthendLeague One · England | 1–2 | League One · England |
| 2008-09-26 | SouthendvLeyton OrientLeague One · England | 3–0 | League One · England |
| 2008-09-20 | CrewevSouthendLeague One · England | 3–4 | League One · England |
| 2008-09-13 | SouthendvHerefordLeague One · England | 1–0 | League One · England |
| 2008-09-06 | CarlislevSouthendLeague One · England | 2–1 | League One · England |
| 2008-08-30 | WalsallvSouthendLeague One · England | 5–2 | League One · England |
| 2008-08-22 | SouthendvBrightonLeague One · England | 0–2 | League One · England |
| 2008-08-16 | MillwallvSouthendLeague One · England | 1–1 | League One · England |
| 2008-08-09 | SouthendvPeterboroLeague One · England | 1–0 | League One · England |
| 2008-05-03 | SouthendvPort ValeLeague One · England | 1–1 | League One · England |
| 2008-04-26 | TranmerevSouthendLeague One · England | 1–0 | League One · England |
| 2008-04-19 | CarlislevSouthendLeague One · England | 1–2 | League One · England |
| 2008-04-12 | SouthendvNorthamptonLeague One · England | 1–1 | League One · England |
| 2008-04-08 | SouthendvBrightonLeague One · England | 2–0 | League One · England |
| 2008-04-05 | CrewevSouthendLeague One · England | 1–3 | League One · England |
| 2008-03-29 | SouthendvWalsallLeague One · England | 1–0 | League One · England |
| 2008-03-24 | SwindonvSouthendLeague One · England | 0–1 | League One · England |
| 2008-03-21 | SouthendvSwanseaLeague One · England | 1–1 | League One · England |
| 2008-03-15 | HuddersfieldvSouthendLeague One · England | 1–2 | League One · England |
| 2008-03-11 | SouthendvNott'm ForestLeague One · England | 1–1 | League One · England |
| 2008-03-08 | SouthendvLutonLeague One · England | 2–0 | League One · England |
| 2008-02-29 | CheltenhamvSouthendLeague One · England | 1–1 | League One · England |
| 2008-02-23 | YeovilvSouthendLeague One · England | 0–3 | League One · England |
| 2008-02-16 | SouthendvBournemouthLeague One · England | 2–1 | League One · England |
| 2008-02-12 | MillwallvSouthendLeague One · England | 2–1 | League One · England |
| 2008-02-09 | SouthendvHartlepoolLeague One · England | 2–1 | League One · England |
| 2008-02-02 | Leyton OrientvSouthendLeague One · England | 2–2 | League One · England |
| 2008-01-29 | SouthendvLeedsLeague One · England | 1–0 | League One · England |
| 2008-01-22 | HartlepoolvSouthendLeague One · England | 4–3 | League One · England |
| 2008-01-19 | BournemouthvSouthendLeague One · England | 1–4 | League One · England |
| 2008-01-12 | SouthendvYeovilLeague One · England | 1–1 | League One · England |
| 2008-01-01 | SouthendvBristol RvsLeague One · England | 0–1 | League One · England |