Just days after the final game of the 2013–14 season saw Joe Dunne's squad immediately begin to change shape. Following club stalwart Karl Duguid's retirement and Clinton Morrison's exit announcement prior to the final game of the season, the next player to leave the Community Stadium was recently appointed club captainBrian Wilson. With Colchester United in the midst of financial cutbacks, the U's were unable to offer Wilson competitive terms, as the defender decided to leave and search for a new club. Following Wilson out the exit door were Academy products Jordan Sanderson and Shaun Phillips, while Ryan Dickson was offered a new deal after his one-year contract expired.
Colchester's first signing of the campaign was young strikerDominic Smith on a one-year contract on 14 May. Smith had been on trial with the U's and had featured during the tail-end of the 2013–14 season for the development squad. He joined following his release from Crewe Alexandra. On 22 May, Dominic Vose signed a contract extension that would tie him to the club until 2016, while Ryan Dickson decided against signing a fresh deal with Colchester in early June, instead opting to join League One rivals Crawley Town on a two-year contract. Academy goalkeeperMark Cousins decided to end his ten year association with the club to sign for Dagenham & Redbridge on a free transfer on 23 June. The U's brought in a trio of players on 1 July to the positions left void by the departing Brian Wilson, Ryan Dickson and Mark Cousins. First, it was announced former Southend United and Gillinghamright-backSean Clohessy had joined the club on a two-year deal. It was then confirmed that left-back Ben Gordon had joined on a free transfer from Ross County. Finally, ex-Dagenham goalkeeper Chris Lewington signed a two-year contract with Colchester to challenge Sam Walker for the number one position, having made almost 150 league and cup appearances for the Daggers.Josh Thompson did enough to prove to manager Dunne that he deserved a new contract, signing a one year deal alongside David Wright on 3 July. On 8 July, Colchester signed former Braintree Town striker Dan Holman on a two-year deal to bolster their attacking options.
Colchester's first friendly for pre-season was an away trip to Brantham Athletic on 12 July. The U's won 4–1, with goals provided by Dominic Vose, Jabo Ibehre and Freddie Sears, with Dan Holman also registering his first goal for Colchester in his first appearance for the club. Their next friendly followed on 15 July, with a game against Heybridge Swifts. Swifts' goalkeeper Danny Sambridge arrived late for the game, which meant Chris Lewington unusually started in goal for Heybridge until Sambridge arrived. Colchester opened the scoring on 16 minutes through Freddie Sears, before triallist loanee George Moncur doubled the lead two minutes later. David Wright then headed home a Dan Holman cross to make it 3–0, until Sears scored from a free kick for a 4–0 half-time lead. As with the Brantham tie, Dunne fielded an entirely different team for the second half, as Gavin Massey scored, shortly followed by Dominic Vose with a solo effort to bring his tally to two goals in two games. Two goals from Jabo Ibehre sealed an emphatic 8–0 victory for Colchester. The U's pre-season tally totalled 16 goals in three games across the space of six days as they defeated A.F.C. Sudbury 4–1 on 17 July at King's Marsh. Goals came from a Freddie Sears penalty, Drey Wright, Sammie Szmodics and Dan Holman. Sears added a further four goals to his pre-season total on 19 July in Colchester's 8–1 win at Leiston. Dan Holman opened the scoring on five minutes with a header, but it wasn't until the 42nd minute that the U's doubled their advantage through Gavin Massey. Sammie Szmodics then made it 3–0 on the stroke of half-time. Leiston pulled a goal back through Gareth Heath on 52 minutes, but substitute Sears scored the first of his four goals two minutes later. He netted his second two minutes after, and his hat-trick came following Drey Wright's goal on 64 minutes, rounding Leiston goalkeeper Danny Gay and producing a sublime finish. The U's completed the scoring in the 87th minute when Alex Gilbey was fouled in the penalty area, and Sears stepped up to covert the spot kick.
Colchester faced Southend United in a behind-closed-doors friendly at Roots Hall on 22 July. A youthful U's lost 2–1 to a strong Shrimpers side, who went two goals ahead through Lee Barnard and Will Atkinson. Frankie Kent pulled a goal back for Colchester, who made eleven substitutions after 70 minutes. The following day, the club hosted its first home game of the pre-season workout, hosting neighbours and rivals Ipswich Town. The Colchester starting eleven featured all four players who had signed over the summer, and also included former Ipswich player Darren Ambrose on loan. Despite having the better chances in the first half, the U's went in at half time 0–0 against their Championship opponents. Less than ten minutes after the interval, Town opened the scoring through Frank Nouble, who doubled their lead just two minutes later. Jack Marriott completed the scoring in a result that ended in identical fashion in 2013–14 pre-season. Colchester were held to a 2–2 draw at Dover Athletic on 25 July. They had fallen behind in the fourth minute when Craig Stone scored from a rebounded shot. The U's went in at half-time 2–1 up, with Sammie Szmodics getting on the end of a Gavin Massey cross after 30 minutes, and a header from Josh Thompson put gave United the lead five minutes before the break. Colchester were denied victory when Nathan Elder equalised in the 78th minute.
The U's featured in a seven-goal thriller at Victoria Road as they came from 3–1 down to win 4–3 on 26 July. Colchester's goalkeeper Lewington faced a trip to his former club, as Colchester also came up against a number of former players, including goalkeeper Mark Cousins, who had made a switch to the Daggers earlier in the summer, and triallist George Porter, who starred for the club on loan in 2013. Macauley Bonne opened the scoring after six minutes, tucking home a rebound from a cross that Dagenham had failed to deal with. However, they equalised on 15 minutes, as Abu Ogogo netted with a header from a corner. Triallist Ashley Hemmings put the Daggers in front just before half-time, and Ashley Chambers scored their third on the hour mark, blasting a 25-yard shot past Lewington. Five minutes later, Colchester began their fightback when Dominic Vose scored from a long range free kick. Vose then scored the U's equaliser on 76 minutes, with a 35-yard shot flying into the net. Jabo Ibehre scored the winner for United just two minutes later. Colchester's next outing was at Luton Town on 29 July, where they battled to a 2–2 draw against their League Two opposition. The Hatters' opened the scoring on 26 minutes after the U's defence failed to clear a parried save from Sam Walker, as Mark Cullen buried the ball from inside the box. Just two minutes later, Colchester drew level after Ibehre's scuffed shot deflected into the net via Luton defender Paul Connolly. Ibehre scored a goal for himself six minutes after the break, slotting past Elliot Justham. However, Luton levelled on 67 minutes through former-Colchester player Luke Guttridge. The clubs final arranged pre-season game followed the Luton match on 30 July, as a young U's squad travelled to Conference South side Bishop's Stortford. After a goalless first half, the Blues opened the scoring within a minute of the restart through Sheldon Sellears. They quickly doubled their lead, with goalscorer Sellears setting up teammate Anthony Church to inflict a 2–0 defeat on the U's.
Following his pre-season training with the club, George Moncur signed on loan until 11 January 2015 on 7 August ahead of the opening fixture against Oldham Athletic the following weekend. On the same day, it was announced that Magnus Okuonghae would be Colchester United's new club captain, with new-boy Sean Clohessy named as vice-captain.
Colchester kicked off their League One campaign at home to Oldham Athletic on 9 August. The Latics' team featured two former Colchester United players, with Brian Wilson featuring having moved north from the U's earlier in the summer, and George Elokobi, who had featured for the club during its stint in the Championship. The U's opened the scoring after seven minutes, with Magnus Okuonghae placing a shot past Oldham goalkeeper Paul Rachubka. However, Oldham equalised through Jonathan Forte on 18 minutes, who then doubled their lead in the 40th minute. Having replaced the injured Craig Eastmond in the first half, George Moncur made his debut for the club a memorable one as he fired a shot into the top corner of the net after 58 minutes to level the scores at 2–2. The scores would remain the same, while new signing Dan Holman received his first taste of League football when he came on as a late substitute for Gavin Massey. On 16 August, the U's travelled to Ashton Gate to take on league favourites Bristol City. Without captain Okuonghae through suspension, and Josh Thompson once again ruled out through injury, a senior starting debut was handed to Frankie Kent. Colchester took the lead in the ninth minute, with George Moncur tapping home his second goal in as many league games. They held on to their slim advantage until half time, but conceded immediately after the interval as Aaron Wilbraham converted a Greg Cunningham cross. He scored his second goal in the 68th minute to hand the Robins a 2–1 lead, heading Wade Elliott's delivery into the back of the net. City held on for their win to leave Colchester 17th in the League One table. Despite dominating their match with nine-man Notts County at Meadow Lane on 19 August, Colchester found themselves on the end of a 2–1 defeat. The U's had been looking to break a winless run of five games against the Magpies, and they had not won at Meadow Lane in their last five visits. They got off to a bad start, conceding after six minutes when Ronan Murray slotted a shot home in the bottom left corner of the goal. County held onto their slender lead until half-time, but with Colchester dominating possession and registering more shots on target than their counterparts, the pressure eventually paid off on 69 minutes when Freddie Sears helped himself to his first goal of the season. However, the celebrations were short-lived as County immediately hit back with a goal from Liam Noble whose shot from outside of the box flew in to the top right corner of the net. The Magpies were able to hold onto their lead, but had both Cieron Keane and Nicky Wroe sent off for second bookable offences. A 1–0 home defeat to Doncaster Rovers on 23 August left the U's still looking for their first win of the season. The result saw them lie third-bottom in the League One table after Kyle Bennett's strike midway through the first half sealed victory for Doncaster. Colchester esnured they ended August with only one point from five league games when Peterborough United visited the Community Stadium on 30 August when they suffered a 3–1 defeat. Goals from Conor Washington and Kgosi Ntlhe in four first-half minutes put the Posh in a commanding position going into the half-time break. Freddie Sears scored his second of the campaign to reduce the deficit to one goal on 64 minutes, but Jermaine Anderson tied up the win for Peterborough 13 minutes from time. Goalscorer Ntlhe saw the red card for a second bookable offence shortly after Peterborough's third goal, but they held on to ensure that Colchester remained without a win in all competitions for the month of August.
Following the clubs poor run of form, manager Joe Dunne left the club by mutual consent on 1 September. Chairman Robbie Cowling acted quickly to replace Dunne by promoting Tony Humes to the position of first-team manager having previously overseen youth development at the club and having guided the under-18 side to a league and cup double during in the 2013–14 season. On 2 September, Humes brought in youngster Byron Lawrence from Ipswich Town on a one-year deal, with Lawrence becoming the first signing under his stewardship. Lawrence had featured on trial for Colchester in the development squad during August. In Humes' first match in charge on 6 September, he took his Colchester side to face fellow strugglers Walsall. He handed Dominic Smith his professional debut when he was sent on as a second half substitute for Gavin Massey. With limited chances for both sides, the game ended 0–0, as the U's picked up their first clean sheet of the season and only their second point in six matches. Colchester picked up their first win of the season when visiting Leyton Orient on 13 September. Up until the half-time break, the score had remained at 0–0, however, U's captain Magnus Okuonghae received his second red card of the season when he was dismissed for serious foul play two minutes before the interval. Despite the disadvantage, Colchester took the lead on 62 minutes with Sanchez Watt netting his first goal of the season when he received a Freddie Sears pass in the centre of the box on a fast break. Eleven minutes later, Sears then doubled the lead to hand Tony Humes his first win as manager. The U's hosted Sheffield United at the Community Stadium for a Tuesday night fixture on 16 September. George Moncur scored his third goal of the season just after the half-hour mark with a header, and Freddie Sears continued his good scoring form when he stabbed the ball home after goalkeeper Mark Howard spilled the ball with 13 minutes on the clock. However, the Blades' sparked a comeback when midfielder Ben Davies struck on 83 minutes, and the scores were levelled just two minutes later through Ryan Flynn. With two minutes remaining until the full-time whistle, Sheffield completed a remarkable six minute salvo when Alex Gilbey fouled Stefan Scougall in the penalty area and Davies stepped up to convert the kick with his second goal of the game. The result left Colchester in the relegation zone and gave Tony Humes his first taste of defeat as first-team manager.
The U's made a number of loan market moves on 19 September. First, Dan Holman joined Conference National club Wrexham on a one-month loan deal in a bid to regain match fitness. Holman's move paved the way for young Cardiff City forward Rhys Healey to sign a loan contract that would run until 20 December. In addition to these moves, development squad striker Nnamdi Nwachuku made an initial one-month loan switch to Isthmian League Premier Division side Leiston. On 20 September, Colchester held Phil Parkinson's Bradford City to a 0–0 draw at the Community Stadium. Despite dominating the match, Colchester could not find the target with a result that left the club 23rd in the League One table.
The U's were drawn against Championship opposition in the first round of the League Cup in the shape of Charlton Athletic. The fixture was held on 12 August at The Valley. Colchester went into the match missing five players, with long-term absentee Tosin Olufemi, David Wright and Sanchez Watt missing out, and Craig Eastmond and Drey Wright also not featuring after collecting knocks in the previous weekend's League One fixture against Oldham Athletic. Joe Dunne's side once again crashed out of the competition at the first hurdle, falling to a heavy 4–0 defeat. The manager handed a debut to goalkeeper Chris Lewington for the fixture in which captain Magnus Okuonghae was sent off for a deliberate handball in the penalty area. Yoni Buyens duly converted from the spot with the sides going into the interval with the score 1–0 to the home side. After the break, former Colchester player Lawrie Wilson scored twice in five second-half minutes to give the Addicks an unassailable 3–0 lead, before Simon Church rounded off the scoring in the 89th minute.
Updated to games played on 20 September 2014.
Source: BBC Sport
Rules for classification: 1) points; 2) goal difference; 3) number of goals scored (C) = Champion; (R) = Relegated; (P) = Promoted; (E) = Eliminated; (O) = Play-off winner; (A) = Advances to a further round.
Only applicable when the season is not finished: (Q) = Qualified to the phase of tournament indicated; (TQ) = Qualified to tournament, but not yet to the particular phase indicated; (RQ) = Qualified to the relegation tournament indicated; (DQ) = Disqualified from tournament.
The draw for the first round was made on 16 August 2014, with Colchester United receiving a bye into the second round. In the second round draw, the U's were handed a home tie against League One rivals Gillingham, with the match set to be played on 7 October.