| 2008-12-28 | ColchestervLeyton OrientLeague One · England | 1–0 | League One · England |
| 2008-12-26 | BrightonvColchesterLeague One · England | 1–2 | League One · England |
| 2008-12-20 | ColchestervScunthorpeLeague One · England | 0–0 | League One · England |
| 2008-12-13 | LeedsvColchesterLeague One · England | 1–2 | League One · England |
| 2008-12-06 | ColchestervHerefordLeague One · England | 1–2 | League One · England |
| 2008-11-29 | NorthamptonvColchesterLeague One · England | 1–2 | League One · England |
| 2008-11-25 | ColchestervYeovilLeague One · England | 1–0 | League One · England |
| 2008-11-22 | PeterborovColchesterLeague One · England | 2–1 | League One · England |
| 2008-11-15 | ColchestervWalsallLeague One · England | 0–2 | League One · England |
| 2008-11-01 | SouthendvColchesterLeague One · England | 3–3 | League One · England |
| 2008-10-25 | ColchestervCarlisleLeague One · England | 5–0 | League One · England |
| 2008-10-21 | ColchestervMillwallLeague One · England | 1–2 | League One · England |
| 2008-10-18 | StockportvColchesterLeague One · England | 1–2 | League One · England |
| 2008-10-11 | CheltenhamvColchesterLeague One · England | 4–3 | League One · England |
| 2008-10-04 | ColchestervBristol RvsLeague One · England | 0–1 | League One · England |
| 2008-09-30 | ColchestervLeicesterLeague One · England | 0–1 | League One · England |
| 2008-09-26 | TranmerevColchesterLeague One · England | 3–4 | League One · England |
| 2008-09-20 | ColchestervMilton Keynes DonsLeague One · England | 0–3 | League One · England |
| 2008-09-13 | CrewevColchesterLeague One · England | 2–0 | League One · England |
| 2008-08-30 | ColchestervOldhamLeague One · England | 2–2 | League One · England |
| 2008-08-23 | SwindonvColchesterLeague One · England | 1–3 | League One · England |
| 2008-08-16 | ColchestervHuddersfieldLeague One · England | 0–0 | League One · England |
| 2008-08-09 | HartlepoolvColchesterLeague One · England | 4–2 | League One · England |