| 2023-12-29 | AFC WimbledonvColchesterLeague Two · England | 5–3 | League Two · England |
| 2023-12-26 | Milton Keynes DonsvColchesterLeague Two · England | 1–0 | League Two · England |
| 2023-12-22 | ColchestervSalfordLeague Two · England | 2–1 | League Two · England |
| 2023-12-16 | WrexhamvColchesterLeague Two · England | 2–1 | League Two · England |
| 2023-12-09 | ColchestervCrawley TownLeague Two · England | 1–2 | League Two · England |
| 2023-11-28 | DoncastervColchesterLeague Two · England | 3–1 | League Two · England |
| 2023-11-25 | ColchestervBarrowLeague Two · England | 1–4 | League Two · England |
| 2023-11-18 | StockportvColchesterLeague Two · England | 2–0 | League Two · England |
| 2023-11-11 | ColchestervSuttonLeague Two · England | 1–1 | League Two · England |
| 2023-11-07 | ColchestervSwindonLeague Two · England | 3–1 | League Two · England |
| 2023-10-28 | AccringtonvColchesterLeague Two · England | 0–1 | League Two · England |
| 2023-10-24 | GrimsbyvColchesterLeague Two · England | 2–3 | League Two · England |
| 2023-10-21 | ColchestervHarrogateLeague Two · England | 1–2 | League Two · England |
| 2023-10-14 | Forest GreenvColchesterLeague Two · England | 5–0 | League Two · England |
| 2023-10-07 | ColchestervMorecambeLeague Two · England | 1–3 | League Two · England |
| 2023-10-03 | Newport CountyvColchesterLeague Two · England | 2–1 | League Two · England |
| 2023-09-30 | ColchestervNotts CountyLeague Two · England | 5–4 | League Two · England |
| 2023-09-23 | CrewevColchesterLeague Two · England | 2–1 | League Two · England |
| 2023-09-16 | ColchestervMansfieldLeague Two · England | 1–1 | League Two · England |
| 2023-09-09 | ColchestervTranmereLeague Two · England | 2–0 | League Two · England |
| 2023-09-02 | WalsallvColchesterLeague Two · England | 1–0 | League Two · England |
| 2023-08-26 | GillinghamvColchesterLeague Two · England | 0–3 | League Two · England |
| 2023-08-19 | ColchestervMilton Keynes DonsLeague Two · England | 2–3 | League Two · England |
| 2023-08-15 | ColchestervAFC WimbledonLeague Two · England | 0–2 | League Two · England |
| 2023-08-12 | BradfordvColchesterLeague Two · England | 2–1 | League Two · England |
| 2023-05-08 | ColchestervMansfieldLeague Two · England | 0–2 | League Two · England |
| 2023-04-29 | DoncastervColchesterLeague Two · England | 1–0 | League Two · England |
| 2023-04-22 | ColchestervSuttonLeague Two · England | 4–1 | League Two · England |
| 2023-04-18 | Crawley TownvColchesterLeague Two · England | 0–0 | League Two · England |
| 2023-04-15 | SalfordvColchesterLeague Two · England | 0–1 | League Two · England |
| 2023-04-10 | ColchestervCreweLeague Two · England | 4–0 | League Two · England |
| 2023-04-07 | StevenagevColchesterLeague Two · England | 1–1 | League Two · England |
| 2023-04-01 | ColchestervNewport CountyLeague Two · England | 0–0 | League Two · England |
| 2023-03-25 | ColchestervTranmereLeague Two · England | 1–1 | League Two · England |
| 2023-03-18 | Leyton OrientvColchesterLeague Two · England | 2–2 | League Two · England |
| 2023-03-11 | ColchestervStockportLeague Two · England | 0–1 | League Two · England |
| 2023-03-04 | BradfordvColchesterLeague Two · England | 2–0 | League Two · England |
| 2023-02-25 | ColchestervNorthamptonLeague Two · England | 0–1 | League Two · England |
| 2023-02-18 | CarlislevColchesterLeague Two · England | 1–0 | League Two · England |
| 2023-02-14 | ColchestervWalsallLeague Two · England | 0–0 | League Two · England |
| 2023-02-11 | GrimsbyvColchesterLeague Two · England | 0–1 | League Two · England |
| 2023-02-04 | ColchestervBarrowLeague Two · England | 1–1 | League Two · England |
| 2023-01-28 | HartlepoolvColchesterLeague Two · England | 1–2 | League Two · England |
| 2023-01-24 | ColchestervSalfordLeague Two · England | 1–1 | League Two · England |
| 2023-01-21 | ColchestervGillinghamLeague Two · England | 0–2 | League Two · England |
| 2023-01-14 | RochdalevColchesterLeague Two · England | 1–2 | League Two · England |
| 2023-01-07 | HarrogatevColchesterLeague Two · England | 1–3 | League Two · England |
| 2023-01-01 | ColchestervSwindonLeague Two · England | 1–0 | League Two · England |