With Arrizabalaga struggling to stay in form during the 2019–20 Premier League season, Caballero was selected as the starting goalkeeper for Chelsea in a cup match against Hull City in late January 2020. Caballero was then the starting goalkeeper for the next four league matches and a Champions League match before Arrizabalaga returned. Caballero played in the 2020 FA Cup Final, a 2–1 loss to Arsenal On 20 May 2020, Caballero had his contract with Chelsea extended by one more year.