Raymond Floyd, 1990 and 1992 Masters
Raymond Floyd won majors in the 60s, 70s and 80s, and had two chances at adding to his major tally in the 90s after a late resurgence in his career. In 1990, Floyd, 47, hooked his second shot on the second playoff hole into the water to hand the green jacket to Nick Faldo. He had a chance at redemption two years later, but was held off by Fred Couples (courtesy, at least in some part, to a lucky break on Augusta's 12th hole), and finished second.