On October 9, 2019, in Game 5 of the National League Division Series, Kendrick hit a grand slam in the 10th inning off Los Angeles Dodgers pitcher Joe Kelly to give the Nationals a 7-3 lead that held up as the final score, advancing the Nationals to the National League Championship Series. It was just the second extra-innings grand slam in MLB postseason history, the other being hit by Nelson Cruz in the 2011 American League Championship Series.