Stewart represented the United States on five Ryder Cup teams (1987, 1989, 1991, 1993, and 1999). He also played for the U.S. on three World Cup teams. His Ryder cup record was 8–9–2. Stewart was known for his patriotic passion for the Ryder Cup, once saying of his European opponents, "On paper, they should be caddying for us." The United States team was 3–1–1 during the five times he played. He was disappointed to miss out in 1995 and 1997, when he failed to qualify automatically and was not chosen as a captain's pick. In the 1999 Ryder Cup, Stewart criticized the heckling of European player Colin Montgomerie. With victory assured for the United States, Stewart conceded a putt (and his own singles match) to Montgomerie on the 18th hole. "This game is about sportsmanship," Stewart said afterwards.