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. Colchester returned to winning ways on 17 September with another 3–0 win against Swindon Town, on this occasion away in the league. Tom Eastman opened the scoring in first-half injury time before a Theo Robinson brace sealed the win. On 21 September, Colchester won 2–1 at home to
Leyton Orient. Kwame Poku scored his debut professional goal after just three minutes, before
Ryan Jackson doubled the U's lead in the 28th minute.
Conor Wilkinson pulled a goal back for the visitors just after half-time but Colchester held on to move them up to tenth in the League Two table. Colchester drew their biggest crowd of the season of 9,481 when they hosted Premier League side
Tottenham Hotspur in the third round of the EFL Cup on 24 September. Colchester had last reached the third round in the
2004–05 campaign. Colchester were dominated by the opposition for much of the game, registering just four shots and none on target while Spurs had 75 per cent possession. Despite this, a resilient U's side held on for 90 minutes with the tie ending goalless and going on to a penalty shoot-out. Dean Gerken in the Colchester goal saved the first penalty from
Christian Eriksen, and despite Jevani Brown's poor
Panenka penalty kick keeping the score level overall,
Lucas Moura hit the bar only for Tom Lapslie to score the winning penalty for the U's. This put them through to the fourth round for the first time since the
1974–75 when they reached the quarter-finals.
October On 5 October, Colchester started the month with a 3–1 win against League Two's bottom club
Stevenage. The visitors opened the scoring with a first-half deflected goal, but Tom Eastman equalised shortly after the break. It was not until the 82nd minute that the U's took the lead after Frank Nouble had been fouled in the penalty area and he stepped up to convert the spot kick. A minute later, he turned provider for Kwame Poku to score his second Colchester goal and seal the victory. After beating the Tottenham Hotspur first-team in the EFL Cup, Colchester hosted their
under-21 side in the EFL Trophy group stage. A Luke Norris headed goal put Colchester ahead on 44 minutes, but the visitors equalised 15 minutes from full time through
Tashan Oakley-Boothe. The game ended 1–1 and the match went to a penalty shoot-out, which Spurs won to claim a bonus point. On 11 October, teenage defender
Ollie Kensdale joined National League South side
Bath City in a month-long loan deal. Colchester visited
Crawley Town on 12 October, and despite taking a first half lead through Luke Prosser, the home side scored twice in the second half to claim victory. On 18 October, Noah Chilvers joined Ollie Kensdale at Bath City in a month-long loan deal. On 19 October, Colchester suffered their second successive defeat, on this occasion a 1–0 reverse against League Two's bottom side
Morecambe. Colchester held league leaders
Crewe Alexandra to a 0–0 draw at
Gresty Road on 22 October, but had the chance to win the game from the penalty spot in the seventh minute of stoppage time. However, Crewe goalkeeper
Will Jääskeläinen saved Frank Nouble's effort after U's forward Theo Robinson had been sent off in an off the ball incident after the penalty had been awarded. Colchester returned to winning ways on 26 October for the first time in three weeks with a 3–1 home win against
Newport County. The visitors were in front after just five minutes, but first-half goals from Ryan Jackson and
Ben Stevenson put the U's in control. A goal from Courtney Senior 15 minutes from the full-time whistle rounded off the victory for Colchester. On 29 October, Colchester reached the quarter-final of the League Cup for only the second time in the club's history, coming from behind to win 3–1 for the second time in three days. Crawley were the hosts and opened the scoring on 20 minutes, but a Luke Norris header two minutes later levelled the score. In the second half, Colchester went ahead after Cohen Bramall's
free kick hit the bar, struck Crawley goalkeeper
Michael Luyambula and went in. Substitute and former-Crawley loanee Luke Gambin sealed victory in the 79th minute, his first goal for the U's.
November Colchester travelled to
Mansfield Town on 2 November where they won 3–2. The U's took an eighth-minute lead through Brandon Comley, but Mansfield equalised on the stroke of half-time. Courtney Senior reinstated Colchester's lead on 74 minutes, before Luke Gambin scored his second in as many games three minutes from full time to secure victory. In the 90th minute,
Omari Sterling-James pulled a goal back for the home side. On 8 November,
Cameron James joined National League South side
Maidstone United on loan for a month. Colchester suffered defeat in the
FA Cup first round for the fourth consecutive season when they lost 2–0 to League One side
Coventry City on 9 November. U's youngsters Luke Ige and Ollie Sims were loaned out to
Witham Town and
Bowers & Pitsea, respectively, on initial 28-day contracts. On 12 November, Colchester played their final group game in the EFL Trophy. They faced Ipswich Town and won 1–0 with a first senior goal from
Ryan Clampin, topping the group in the process. Colchester were held to a 1–1 draw at
Cheltenham Town on 23 November. Luke Norris scored his fifth league goal of the season to hand the visitors the lead, but in the second half, Dean Gerken fouled
Reuben Reid in the penalty area and
Conor Thomas converted to equalise.
December On 3 December, Colchester were defeated in the second round of the EFL Trophy at home to Stevenage in front of a crowd of just 959. Stevenage led 2–0 after half an hour of play, but the home side pulled a goal back in the second half from a
Chris Stokes own goal. On 7 December, Colchester earned their first win in almost a month with a 93rd-minute winner against
Salford City in the first-ever meeting between the two clubs. Harry Pell scored his first goal of the season with an injury time header. Midfielder Diaz Wright joined
National League side
Dagenham & Redbridge on loan until 6 January 2020. Also leaving the club on loan was fellow midfielder Tyrique Hyde, who joined
Dartford in the National League South for one month. After falling behind by two goals in their League Two game at
Scunthorpe United on 14 December, Colchester battled back in the second half to claim a 2–2 draw. Former Colchester loanee
Abo Eisa scored late in the first half for the home side, then
Kevin van Veen doubled Scunthorpe's advantage two minutes into the second half. Luke Norris scored to reduced the deficit just before the hour mark, and Luke Prosser scored his second of the season four minutes later to earn a point for the U's. Colchester travelled to
Old Trafford for the first time in their history to face
Manchester United in the EFL Cup quarter-final. The visitors held their Premier League opposition in the first half, going in to the interval at 0–0. In the second half, it took
Marcus Rashford six minutes to open the scoring, and five minutes later, Ryan Jackson scored an own goal to double United's lead.
Anthony Martial added a third on 61 minutes to complete the scoring. Colchester continued their good run of league form with a commanding 3–0 win over
Carlisle United at the Community Stadium on 21 December.
Nathaniel Knight-Percival's own goal in the 26th minute put the U's 1–0 up and Callum Harriott's first goal since his return to the club doubled Colchester's advantage in the 41st minute. In the second half, Cohen Bramall registered his first goal in the
English Football League with a well taken free kick seven minutes after the restart to seal the victory. In the early League Two kickoff on Boxing Day, Colchester beat Leyton Orient 3–1 at
Brisbane Road to move up to fourth in the table. Theo Robinson gave the U's a 1–0 lead after 41 minutes, then Harry Pell doubled Colchester's lead in the 64th minute. Orient pulled a goal back four minutes from time, but Robinson added a second for himself and scored Colchester's third goal in the 91st minute. Fourth-placed Colchester hosted second-placed
Exeter City in their final game of 2019 on 29 December. The visitors took an eighth-minute lead through
Jake Taylor, but Harry Pell levelled the score after 16 minutes to earn his second goal in as many games. After the break, Theo Robinson put the U's in front with his third goal in two games. Tom Lapslie was sent off for a foul in the penalty area and denying a goalscoring opportunity, a penalty which substitute
Ryan Bowman converted. Colchester held on with ten men to draw 2–2.
January Colchester maintained their unbeaten run with a 1–1 draw with Crawley on New Year's Day. Frank Nouble's fourth goal of the season in the 64th minute was later cancelled out by a Luke Prosser own goal. On 4 January, Jevani Brown left the club to join League Two rivals Forest Green Rovers on loan until the end of the season, having played 17 games for the U's but only five in the league. Also on 4 January, Colchester were held to a disappointing 0–0 draw against ten-man, bottom of the table Stevenage.
Tom Soares had been sent off for the home side in the 19th minute, but a dominant Colchester could not get the ball past Stevenage goalkeeper
Paul Farman. On 6 January, Percy Kiangebeni joined
Southern League Premier Division South side
Hendon on loan for a month. On 8 January, Tyrique Hyde extended his loan spell at Dartford for a further month. On 10 January, both Cameron James and Diaz Wright joined National League South side
Welling United on loan for one month. Colchester were held to a 1–1 draw on 11 January at League Two's bottom club Morecambe. The U's had taken a 35th-minute lead through Frank Nouble, but were pegged back on 69 minutes. Ryan Jackson was then sent off seven minutes from time for a second booking. On 14 January, Colchester confirmed the signing of Theo Robinson on loan from Southend until the end of the season. On 18 January, Plymouth Argyle defender
Tafari Moore joined Colchester on loan until the end of the season. He went straight into the U's squad to face Macclesfield Town the same day. Later that day, Moore played 60 minutes as Colchester ended a streak of four consecutive draws to record a 2–1 victory. Callum Harriott opened the scoring after 14 minutes, before the lead was doubled following a
Fiacre Kelleher own goal. The visitors reduced the deficit in the second half but the U's held on to extend their unbeaten run to 13 games. Colchester were held to a 0–0 draw at home by
Bradford City on 21 January. Their game in hand to clubs around them meant they moved back into the play-off places. On 25 January, midfielder Louis Dunne joined Southern League Premier Division South side
Farnborough on loan until the end of February. Colchester moved up to fifth in the League Two table with a 0–0 draw at second-placed Exeter City on 25 January to record their sixth draw in seven games. The U's hosted league leaders Swindon Town on 28 January. The visitors took the lead three minutes after half-time, but Luke Norris scored against his old club to level the score on 74 minutes. Fifteen minutes later and Colchester had taken a 3–1 lead following a Theo Robinson brace in the 85th and 89th minutes. The match finished 3–1 to the U's as they recorded their third victory of the season against Swindon.
February Colchester's unbeaten run, stretching back to October, was finally ended on 1 February to managerless Cambridge United. Similar to Colchester's August home defeat to Cambridge, Luke Norris had given the U's the lead, but two goals within the space of 70 seconds late in the second half ended their 16-game streak. On 5 February, the club announced the departure of Junior Ogedi-Uzokwe to
Israeli Premier League side
Hapoel Hadera on a permanent contract. The U's bounced back from their defeat to Cambridge in impressive style, beating Plymouth Argyle 3–0 on 8 February. Argyle had started the day in the automatic promotion positions, but three first-half goals sealed victory for the home side. Ben Stevenson opened the scoring for Colchester after 14 minutes, then Theo Robinson headed in his tenth goal of the season on the half-hour mark. Six minutes later, he earned himself a brace to record a convincing victory. On 11 February, Colchester were beaten at home by Grimsby Town. After taking the lead through captain Luke Prosser after 17 minutes,
Charles Vernam scored for the away side four minutes later. The U's retook the lead three minutes before half time with Theo Robinson's twelfth goal for the club. However, Vernam scored two goals in the space of three second-half minutes to snatch a victory for Grimsby. Colchester fell to their heaviest league defeat of the season on 15 February when they were beaten 3–0 at Port Vale. After leaving league rivals Macclesfield Town in January, defender
Miles Welch-Hayes on 21 February on a free transfer. He signed a contract until summer 2022. On 23 February, Colchester won their first match in three games with a 2–1 victory at Salford City. Kwame Poku's solo effort put the U's ahead, before Callum Harriott doubled the advantage after 41 minutes. Two minutes later, the home side pulled a goal back through
Ashley Hunter, but the visitors held on for the win. On 29 February, Colchester dropped out of the play-off places and had Omar Sowunmi sent off as they fell to a 2–0 home defeat to Cheltenham Town.
Season postponement Colchester made a quick return to the play-off positions with a convincing 3–0 away win at Carlisle United on 7 March. Kwame Poku opened the scoring for the U's on 41 minutes, and the lead was doubled by Luke Norris two minutes later. Poku then earned himself a brace in the 59th minute. On 13 March, the EFL suspended the season until 3 April at the earliest in light of the
COVID-19 pandemic. On 3 April, the EFL provided an update to the postponement of the season by suspending all football indefinitely until matches were safe to resume. On 27 April, two days after they were scheduled to have played their final game of the 2019–20 season, Colchester United became the first English Football League team to announce the release of first-team players in light of the COVID-19 pandemic. Chairman Robbie Cowling announced that four first-team players, namely Brandon Comley, Ryan Jackson, Frank Nouble and club captain Luke Prosser, would not be offered new deals once their contracts expired at the end of June. This was despite the fact that Cowling admitted under normal circumstances he "would have been determined to re-sign". The following day, the club released a list of twelve further players who would not be offered new deals on the expiry of their current contracts. These included Dean Ager, Callum Anderson, Jamal Campbell-Ryce, Louis Dunne, Chandler Hallett, Tyrique Hyde, Luke Ige, Tariq Issa, Cameron James, Callum Jones, Percy Kiangebeni and Bailey Vose. On 9 June, League Two clubs voted in favour of ending the season with immediate effect. As Colchester were placed sixth in the League Two table, they were confirmed a
play-off place, with the U's set to face Exeter City in the
semi-finals. Colchester played their play-off semi-final first leg at an empty Colchester Community Stadium on 18 June. The hosts won the tie 1–0 through a Cohen Bramall free-kick late in the second half. In the play-off semi-final second leg on 22 June, Colchester were beaten 3–1 after
extra time, with Exeter heading to the
Wembley final with a 3–2 aggregate victory. The hosts had taken an early lead, before taking control of the tie with a second goal just before the hour mark. Courtney Senior levelled the score on aggregate 2–1 after 78 minutes, before the tie went to extra time. With nine minutes remaining, Exeter scored again to progress to the final and spelt another season in League Two for the U's. ==Players==