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.