Hill played in 40 games for the Yankees, mostly as a designated hitter. He hit 16 home runs in a rotating designated hitter role and was added to the postseason roster. He played in four games in the 2000 American League Division Series against the Oakland A's and was 1 for 12 with 2 runs batted in. In the 2000 American League Championship Series against the Seattle Mariners, Hill played in two games and went 0 for 2, striking out in both of his plate appearances. In the 2000 World Series against the New York Mets, Hill played in three games going 0 for 3. He earned a World Series ring when the Yankees defeated the Mets in five games.