He was offered a new one-year contract by Everton at the end of the 2018–19 season. On his first start of the 2019–20 season, on 18 December 2019, Baines scored the equalizer from 25 yards against Leicester City in the 91st minute of an EFL Cup tie. The match ended in a 2–2 draw before Everton eventually lost on penalties, with Baines having his spot kick saved. At the conclusion of the season Baines announced his retirement from professional football.