In the Championship Series, he allowed one hit in of an inning. However, he rebounded in the 1999 World Series, striking out the only batter he faced. On November 5, he was granted free agency, but re-signed with the Yankees on November 29. In 2000, he was 2–3 with a 4.10 ERA over 69 games. He pitched in four innings of one-hit ball in the Division Series and did not pitch in the Championship Series. In the 2000 World Series, he earned two wins in four games. In 2001, he was 9–4 with a 2.58 ERA and was selected to the 2001 All-Star team. He pitched in all three games of the 2001 American League Division Series and in two games of the 2001 American League Championship Series. He pitched in five games of the 2001 World Series.