In Game 3 of the World Series against the Chicago Cubs, Miller was credited with his first World Series win in a 1–0 victory. After striking out three of four batters faced in innings, he reached 15 consecutive scoreless innings in the 2016 playoffs, surpassing Mariano Rivera and Goose Gossage to set the record for relief pitchers in a single postseason. In Game 4, he struck out two Cubs hitters, bringing his 2016 playoff total to 29, and surpassing Francisco Rodríguez' total of 28 in the 2002 postseason for the all-time record among relievers in a postseason. Another strikeout record Miller set was to strike out at least three batters each in seven different appearances, all in the 2016 postseason, and more than other MLB reliever. Dexter Fowler homered off Miller in Game 5, ending his scoreless streak at 17 innings in the 2016 playoffs and to commence his postseason career. In Game 7, Miller allowed five batters to reach base and two runs to score in innings as the Indians lost the game and Series. Miller's strikeout record for relievers in a single postseason reached 30, and other single-postseason records he set for relievers in 2016 were innings () and multi-inning appearances (10). In spite of finally succumbing in pivotal Game 7 to the Cubs' offense, Miller was named the 2016 Esurance MLB/This Year in Baseball Award winner for Best Postseason Major Leaguer.