 Jackson made one appearance in the 2018–19 season, in a 2–0 loss to Gillingham in the opening game of the season.Jackson signed for Ipswich Town on 9 August 2018 on a three-year deal (with an option of a further 12 months) for an undisclosed fee.The move reported to cost £1 million, which was described by the "Lancashire Telegraph" as "Accrington Stanley's first million pound sale", and saw him reunited with manager Paul Hurst, having previously played under him at Grimsby Town.