Mark Cousins decided to end his ten-year association with the club to instead sign for Dagenham & Redbridge on 23 June. On 1 July, Colchester brought in a trio of new players to fill the void left by the departing Cousins, Dickson, and Wilson. Former Southend United and Gillingham right-back Sean Clohessy joined the club on a two-year deal, Ben Gordon signed on a free transfer from Ross County, and former Dagenham & Redbridge goalkeeper Chris Lewington also signed a two-tear contract. Josh Thompson and David Wright signed new one-year deals on 3 July, and on 8 July, Colchester signed former Braintree Town striker Dan Holman on a two-year deal. Colchester played their first game of pre-season on 12 July against Brantham Athletic. The U's won 4–1 with goals from Dominic Vose, Jabo Ibehre, Freddie Sears and Dan Holman. Three days later they played Heybridge Swifts as triallist George Moncur, David Wright, and a brace from Sears gave them a 4–0 half-time lead. In the second-half, they continued the scoring with goals registered by Gavin Massey, Vose and an Ibehre brace sealed an 8–0 win. They then put four past AFC Sudbury on 17 July with Sears, Drey Wright, Sammie Szmodics and Holman the scorers. Freddie Sears continued his goalscoring for on 19 July as Colchester won 8–1 at Leiston. He scored four, while Holman, Massey, Szmodics and Drey Wright scored the rest. On 23 July, Colchester played their first home friendly of pre-season against neighbours Ipswich Town. Town scored twice in the first twelve minutes of the second-half through Frank Nouble while Jack Marriott added a third later on for the visitors. Colchester were held to a 2–2 draw at Dover Athletic on 25 July, Josh Thompson and Sammie Szmodics the scorers, before a 4–3 victory over Dagenham Redbridge on 26 July. Macauley Bonne scored his first goal of pre-season, but the U's found themselves 3–1 down at the hour mark. Five minutes later, they began their fight back, as Vose scored once and then scored the equaliser on 76-minutes. Jabo Ibehre scored the U's winner two minutes later. On 29 July, Colchester faced Luton Town, where they were held to a 2–2 draw following a Paul Connolly own goal and a Jabo Ibehre goal. The club's final pre-season friendly was a 2–0 defeat at Conference South side Bishop's Stortford on 30 July. On 7 August, after training with