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 a season that was severely disrupted by the COVID-19 pandemic, Colchester reached the play-offs after the season was drawn to an early close. The U's occupied a play-off spot when the season was postponed on 13 March 2020. The campaign officially ended on 9 June following a vote by all League Two member clubs. Final league positions were determined on a points-per-game basis, and Colchester's 1.57 points per game was enough to secure sixth position in the league and the third of four play-off spots.
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.
Colchester equalled their best-ever performance in the EFL Cup, reaching the quarter-finals. After dispatching of League Two rivals Swindon Town in the first round, the U's travelled to Premier League Crystal Palace in round two. Their resolute defending took the tie to a penalty shoot-out which they won 5–4. In the third round, Colchester hosted further Premier League opposition, with Tottenham Hotspur visiting the Colchester Community Stadium. Again, Colchester's staunched defending took the tie to penalties and they went on to win 4–3. In the fourth round, Colchester beat league rivals Crawley Town 3–1 to set up a trip to Old Trafford to take on Manchester United. Three second-half goals were enough for the home side to seal a convincing victory.
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.
Colchester's FA Cup campaign ended in the first round with a home defeat by League One side Coventry City.
Season overview Preseason Colchester's place in League Two for the 2019–20 season was confirmed on the final day of the 2018–19 season on 4 May 2019 after a dramatic late goal for Newport County ensured they finished ahead of the U's in seventh place achieving a place in the play-offs.
The club announced the first departures of the close season on 14 May when twelve under-23 and Academy graduates were not offered new deals. These players included David Agboola, Aaron Barnes, George Brown, Ken Charles, Noah Chesmain, Chris Forino, Arjanit Krasniqi, Eoin McKeown, Paul Rooney, Decarrey Sheriff, Sam Warde and Will Wright.
On 17 May, young midfielder Kwame Poku signed his first professional contract, joining United from Worthing following a successful trial at the end of the 2018–19 season.
On 20 May, Colchester announced that all out of contract players had been offered new deals, except for forward Mikael Mandron, who was allowed to leave the club after two years and 95 appearances, and winger Ryan Gondoh, who had spent the end of last season on loan at Halifax Town.
Brennan Dickenson opted against signing a new contract with Colchester, instead signing for newly promoted League One club Milton Keynes Dons on 30 May.
On 7 June, Colchester announced the signing of former Leicester City under-23 midfielder Sammie McLeod on a two-year contract, joining from Maldon & Tiptree to link up with the U's under-23 side.
On 11 June, forward Junior Ogedi-Uzokwe, who had been on loan at Derry City until 1 June, had his contract extended by a further year after Colchester activated a clause in his contract. He would remain on loan with Derry until the end of the 2019 League of Ireland Premier Division season on 19 November.
Long-serving defender Tom Eastman agreed a two-year contract extension on 13 June.
On 18 June, Colchester signed former VfB Stuttgart defender Danny Collinge on a two-year contract.
Sam Saunders ended his short association with the club on 21 June by announcing his retirement from playing at the age of 35.
After making 141 appearances for the club, defender Frankie Kent left Colchester to sign for League One Peterborough United for an undisclosed fee on 22 June.
On 26 June, Colchester signed Malta international winger Luke Gambin on a two-year contract from Luton Town.
Sammie Szmodics ended a 16-year association with Colchester United on 28 June when he signed for Championship side Bristol City on a three-year deal in an undisclosed compensation deal after his U's contract had expired.
On 1 July, Colchester made several movements in the transfer market. First, they announced Diaz Wright had signed a one-year contract extension with the club. Then, winger Michael Fernandes arrived from Farnborough on a two-year deal, Next, it was announced goalkeeper coach and player Rene Gilmartin had opted to leave the U's to join Bristol City, before announcing the signing of Colchester-born Yeovil Town defender Omar Sowunmi on a two-year contract for an undisclosed fee.
On 2 July, Colchester announced that TEXO Scaffolding would be the new front of home shirt sponsors for kits for the next three seasons. Later the same day, the club announced the signing of Denmark youth international Matthew Weaire from Brighton & Hove Albion on a two-year contract.
On 3 July, Luke Ige arrived from Aston Villa on a one-year contract to join up with the Under-23 squad.
On 4 July, Colchester made a double signing with Cambridge United forward Jevani Brown arriving on a two-year contract for an undisclosed fee, while Paris Cowan-Hall later arrived at the club following his release from Wycombe Wanderers. The winger also signed a two-year deal with the U's.
Colchester started their pre-season friendlies with a game at Isthmian League Premier Division side Bowers & Pitsea on 5 July where they ran out 2–0 winners. The second-half goals were scored by Louis Dunne and Luke Norris.
In the U's second pre-season friendly on 9 July, they took on Dulwich Hamlet of the National League South. Colchester again won 2–0, with second-half goals from Courtney Senior and summer signing Omar Sowunmi.
On 13 July, Dean Gerken signed for Colchester following his release from Ipswich Town at the end of the 2018–19 season. He had been training with the U's and signed ahead of their friendly with Cefn Druids the same day.
New signing Gerken played the opening 45 minutes as the U's beat the Welsh side 3–0 with goals from Andre Hasanally in the first half, and Omar Sowunmi and Luke Norris in the second half.
On 16 July, Colchester won 3–0 at Wealdstone with goals coming from three new signings; Paris Cowan-Hall, Michael Fernandes and Luke Gambin.
On 19 July, young winger Todd Miller left the club to join Premier League side Brighton & Hove Albion, with the U's expected to receive compensation for the teenager. The same day, in their first home friendly of pre-season, Colchester suffered a 5–0 defeat to neighbours and rivals Ipswich Town. The visitors led 1–0 going into half-time, with four goals arriving in the second half.
After turning down a new contract with the club, goalkeeper Dillon Barnes signed for Championship club Queens Park Rangers on a two-year contract on 22 July.
On 23 July, Charlton Athletic won 2–1 with a late goal in the U's latest pre-season friendly after Luke Norris had handed the home side the lead early in the second half.
In Colchester's final pre-season friendly, Luke Norris scored again to secure a late 1–1 draw with Dover Athletic on 27 July.
August On the eve of the season opener against Port Vale, Colchester signed former Arsenal left-back Cohen Bramall on a two-year contract.
Colchester were held to a 1–1 draw by Port Vale at the Colchester Community Stadium on 3 August. The visitors took the lead through a Tom Pope penalty in the fifth minute, but the U's equalised through Luke Norris on the stroke of half-time.
Plymouth Argyle hosted the U's on 10 August and won 1–0 with a second-half goal from Antoni Sarcevic.
The U's earned their first victory of the season on 13 August in their EFL Cup first round tie with Swindon Town. On the back of a goalless first half, both teams had a man sent off for violent conduct in the 62nd minute, with Cohen Bramall shown red for Colchester and Jerry Yates for Swindon. Tom Eastman broke the deadlock in the 77th minute, before substitute Courtney Senior doubled the lead in the second minute of injury time. Fellow substitute Brandon Comley added a third in the seventh minute of injury time to complete the 3–0 victory and see the U's reach the second round for the first time since 2010.
On 17 August, Colchester hosted Cambridge United in the league. A ninth minute Luke Norris penalty gave the U's a 1–0 lead going into the interval, but two Cambridge goals in the second half left Colchester to a 2–1 defeat.
Ipswich Town confirmed the signing of Kane Vincent-Young on 19 August for an undisclosed fee reportedly in the region of £500,000. He left the U's to sign a four-year deal with Town with the option of a further year.
Colchester continued their winless run with another second-half collapse against Grimsby Town on 20 August. Frank Nouble and Luke Norris had given the U's a 2–0 first-half lead, but goals for Grimsby in the 48th and 87th minutes succumbed them to a draw and more dropped points.
On 24 August, the U's picked up their first league win of the season, beating Northampton Town 1–0 courtesy of a Luke Norris penalty, who racked up his fourth goal in five league matches.
In the second round of the EFL Cup on 27 August, Colchester travelled to Premier League Crystal Palace. Following a goalless 90 minutes, the match went to a penalty shoot-out. Andros Townsend stepped up to take the first penalty for the hosts, but his effort was saved by Dean Gerken in the U's goal. Each of the following penalties were scored by their takers, and U's Academy product Noah Chilvers converted the decisive spot kick to send Colchester through to the third round and their first win in the League Cup against top-flight opponents since 1979.
On 28 August, Colchester signed young Bristol City striker Freddie Hinds on loan until January.
On 29 August, the U's signed another striker with the arrival of Southend United's Theo Robinson on loan until January.
After making his first-team debut on the opening weekend of the season, Andre Hasanally signed his first professional contract with the club on 30 August, signing until June 2022.
Colchester rounded out August with a 1–0 win at Oldham Athletic on 31 August. Frank Nouble's strike on the stroke of half-time proved to be the difference between the sides.
September On 2 September, transfer deadline day, Colchester signed young Charlton Athletic midfielder Brendan Sarpong-Wiredu on loan until January, with injuries ruling out Tom Lapslie, Harry Pell and Diaz Wright, and with Brandon Comley and Luke Gambin on international duty.
Sarpong-Wiredu and Kwame Poku both made their debuts on 3 September in Colchester's 3–2 EFL Trophy win against Gillingham. Paris Cowan-Hall scored his first goal for the U's after just eight minutes, before Gillingham equalised. Theo Robinson then scored his first goal for the club after 55 minutes to put the visitors back in front, before Cowan-Hall recorded his second goal of the evening to put Colchester 3–1 up. Former U's player Mikael Mandron pulled a goal back for Gillingham but Colchester held on for victory.
On 5 September, Colchester signed former loanee winger Callum Harriott on a two-year contract following his release from Reading during the summer.
On 7 September, Colchester were held to a goalless draw by Walsall at the Community Stadium.
On 14 September, Colchester were beaten 1–0 at Forest Green Rovers following a Luke Prosser own goal.