In the 2018 MLB playoffs, Benintendi recorded the final outs to seal victories for the Red Sox in Games 4 and 5 of the 2018 American League Championship Series, the first of the two a diving effort to prevent a bases-loaded hit in a two-run game. The Red Sox won the World Series over the Los Angeles Dodgers, giving Benintendi his first championship title. In the World Series Benintendi had 4 hits in Game 1 and hit .333 in the Fall Classic.