Town right-back Elliott Hewitt joining for one month, while David Fox signed a short-term deal after training with the club. Having received a bye in the first round, Colchester crashed out of the Football League Trophy on penalties following a 3–3 draw with Gillingham on 7 October. Drey Wright scored his first goal of the season to open the scoring on 17-minutes, but Brennan Dickenson later equalised. Sanchez Watt made it 2–1 from the penalty spot after Rhys Healey had been fouled in the area, but Bradley Dack allowed the visitors to equalise once again. They then took the lead with 16-minutes remaining when Antonio German scored. Freddie Sears scored a late equaliser, meaning the match went to a penalty shoot-out. George Moncur and Tom Eastman missed their penalties for Colchester as Gillingham won 4–2. Having not featured under Tony Humes, Jabo Ibehre was allowed to leave the club on loan to Oldham on 9 October. The same day, youth team graduate Sammie Szmodics signed a -year contract extension with the club. On 11 October, Colchester came from behind to beat Fleetwood Town 2–1 courtesy of a Gavin Massey brace. After scoring a brace in his previous game, Massey, alongside defenders Tom Eastman and Frankie Kent, all signed contract extensions with the club on 16 October. Eastman agreed a deal until 2016, Massey until 2017, and Kent until 2018. On 18 October, Colchester were held to a 1–1 draw by Scunthorpe United at Glanford Park, Freddie Sears with the U's goal. On 21 October, Colchester hosted Chesterfield. The visitors scored in controversial fashion with less than a minute on the clock after Frankie Kent had been floored by a powerful strike in the face. Referee Darren Sheldrake allowed play to continue as Sam Clucas scored. At half-time Rhys Healey replaced George Moncur and scored within five minutes of his arrival. Four minutes from the full-time whistle, Freddie Sears scored once again to earn all three points for Colchester. Dan Holman was loaned out once again on 24 October, on this occasion to Aldershot Town for one month. Joining him in leaving the club on loan was Josh Thompson, yet to appear this season. He joined League Two's bottom club Tranmere Rovers on loan until January. Colchester earned a 2–2 draw at Swindon Town on 25 October. Former U's loanee Michael Smith had given his side the lead in the first-half,