Despite rumors of a potential move to the MLS, in March 2019 Chambers committed his future to the club and signed a new two-year deal, keeping him at the club until 2021. Hurst was sacked and replaced by Paul Lambert, who was unable to reverse Ipswich's poor form, and the club was relegated to EFL League One.
Chambers' decision to commit to the team in March 2019 was a significant factor in ensuring his continued involvement with the club until 2021. Nevertheless, the subsequent appointment of Paul Lambert and Ipswich's poor performance ultimately led to the club being demoted to EFL League One.