| 1996-04-02 | ColchestervRochdaleLeague Two · England | 1–0 | League Two · England |
| 1996-03-30 | HartlepoolvColchesterLeague Two · England | 2–1 | League Two · England |
| 1996-03-23 | ColchestervTorquayLeague Two · England | 3–1 | League Two · England |
| 1996-03-19 | ColchestervCambridgeLeague Two · England | 2–1 | League Two · England |
| 1996-03-16 | ScarboroughvColchesterLeague Two · England | 0–0 | League Two · England |
| 1996-03-09 | ColchestervBuryLeague Two · England | 1–0 | League Two · England |
| 1996-03-02 | Leyton OrientvColchesterLeague Two · England | 0–1 | League Two · England |
| 1996-02-27 | ChestervColchesterLeague Two · England | 1–1 | League Two · England |
| 1996-02-24 | ColchestervDarlingtonLeague Two · England | 1–1 | League Two · England |
| 1996-02-17 | PrestonvColchesterLeague Two · England | 2–0 | League Two · England |
| 1996-02-10 | ColchestervWiganLeague Two · England | 1–2 | League Two · England |
| 1996-02-06 | ColchestervScarboroughLeague Two · England | 1–1 | League Two · England |
| 1996-02-03 | LincolnvColchesterLeague Two · England | 0–0 | League Two · England |
| 1996-01-30 | WiganvColchesterLeague Two · England | 2–0 | League Two · England |
| 1996-01-20 | PlymouthvColchesterLeague Two · England | 1–1 | League Two · England |
| 1996-01-13 | ColchestervBarnetLeague Two · England | 3–2 | League Two · England |
| 1996-01-01 | TorquayvColchesterLeague Two · England | 2–3 | League Two · England |
| 1995-12-26 | ColchestervLeyton OrientLeague Two · England | 0–0 | League Two · England |
| 1995-12-23 | BuryvColchesterLeague Two · England | 0–0 | League Two · England |
| 1995-12-16 | ColchestervScunthorpeLeague Two · England | 2–1 | League Two · England |
| 1995-12-09 | HerefordvColchesterLeague Two · England | 1–1 | League Two · England |
| 1995-11-25 | ColchestervMansfieldLeague Two · England | 1–3 | League Two · England |
| 1995-11-18 | DoncastervColchesterLeague Two · England | 3–2 | League Two · England |
| 1995-11-04 | ColchestervExeterLeague Two · England | 1–1 | League Two · England |
| 1995-10-31 | FulhamvColchesterLeague Two · England | 1–1 | League Two · England |
| 1995-10-28 | CardiffvColchesterLeague Two · England | 1–2 | League Two · England |
| 1995-10-21 | ColchestervNorthamptonLeague Two · England | 1–0 | League Two · England |
| 1995-10-14 | RochdalevColchesterLeague Two · England | 1–1 | League Two · England |
| 1995-10-07 | ColchestervHartlepoolLeague Two · England | 4–1 | League Two · England |
| 1995-09-30 | ScunthorpevColchesterLeague Two · England | 1–0 | League Two · England |
| 1995-09-23 | ColchestervHerefordLeague Two · England | 2–0 | League Two · England |
| 1995-09-16 | DarlingtonvColchesterLeague Two · England | 2–2 | League Two · England |
| 1995-09-12 | ColchestervPrestonLeague Two · England | 2–2 | League Two · England |
| 1995-09-09 | ColchestervChesterLeague Two · England | 1–2 | League Two · England |
| 1995-09-02 | GillinghamvColchesterLeague Two · England | 0–1 | League Two · England |
| 1995-08-29 | CambridgevColchesterLeague Two · England | 3–1 | League Two · England |
| 1995-08-26 | ColchestervLincolnLeague Two · England | 3–0 | League Two · England |
| 1995-08-19 | BarnetvColchesterLeague Two · England | 1–1 | League Two · England |
| 1995-08-12 | ColchestervPlymouthLeague Two · England | 2–1 | League Two · England |
| 1995-05-06 | ChesterfieldvColchesterLeague Two · England | 2–2 | League Two · England |
| 1995-04-29 | ColchestervCarlisleLeague Two · England | 0–1 | League Two · England |
| 1995-04-22 | ColchestervLincolnLeague Two · England | 1–2 | League Two · England |
| 1995-04-17 | NorthamptonvColchesterLeague Two · England | 1–1 | League Two · England |
| 1995-04-15 | ColchestervFulhamLeague Two · England | 5–2 | League Two · England |
| 1995-04-11 | GillinghamvColchesterLeague Two · England | 1–3 | League Two · England |
| 1995-04-08 | HerefordvColchesterLeague Two · England | 3–0 | League Two · England |
| 1995-04-01 | WalsallvColchesterLeague Two · England | 2–0 | League Two · England |
| 1995-03-25 | ColchestervScarboroughLeague Two · England | 0–2 | League Two · England |
| 1995-03-18 | ColchestervExeterLeague Two · England | 3–1 | League Two · England |
| 1995-03-11 | HartlepoolvColchesterLeague Two · England | 3–1 | League Two · England |