The 2019–20 season was Colchester United's 83rd season in their history and their fourth successive season competing in League Two. Along with competing in League Two, the club participated in the FA Cup, EFL Cup and EFL Trophy. In their play-off semi-final first leg with Exeter City, the U's won 1–0 at home, but lost 3–2 on aggregate following a 3–1 extra time defeat at St James Park. In the EFL Trophy, Colchester won their first group with wins over Gillingham and local rivals Ipswich Town, but were defeated in the second round by Stevenage.