 Ipswich Town managed to beat off competitions from "a number of Sky Bet Championship clubs" to sign him.He made his Ipswich Town debut on 11 August, coming on as a substitute for Ellis Harrison, in a 1–0 loss against Rotherham United two days after signing for the club.Three days later, on 14 August 2018, Jackson scored his first goal for the club against Exeter City in the first round of the EFL Cup, with Ipswich eventually losing 4–2 in a penalty shootout after the game finished 1–1.