In 2000, Leiter made the All-Star team once again going 16–8 with a 3.20 ERA and 200 strikeouts. The Mets made the playoffs again in 2000 and this time reached the World Series. Leiter started Game 1 of the 2000 World Series at Yankee Stadium and Game 5 at Shea Stadium. Although he managed to achieve a 2.87 ERA and 16 strikeouts in innings, the Mets lost both games he started and eventually lost the World Series 4 games to 1. He was booed by Yankee fans when presented that year's Roberto Clemente Award prior to Game 2 of the World Series. Leiter was the second New York Met to be honored with the award. During the 2000 season, he pitched in the All Star game, and gave up a single to Derek Jeter.