Leonard qualified for the United States Ryder Cup team in 1997, 1999, and 2008. In the 1999 event, Leonard made a putt for birdie on the 17th hole to complete a remarkable comeback by the U.S. team on the final day. The victory was somewhat marred by the celebration following Leonard's putt, when other U.S. players, their wives, and a few fans ran onto the green even though Leonard's opponent, José María Olazábal, still had an opportunity to match Leonard on the hole.