In the 2019 postseason, Bregman enjoyed an excellent ALDS against the Tampa Bay Rays, batting .353/.450/.647 with two doubles, one home run, three walks, and two RBIs. Bregman's bat went ice cold in the ALCS and first three games of the World Series, though, as he struggled through a 4-for-31 (.129) slump with only one home run and three RBIs. Bregman broke out of his slump in Game 4 of the World Series by hitting 3-for-5 with a grand slam and 5 RBIs in an 8-1 Astros win that tied the series at 2-2. The Astros eventually lost the series in seven games.