On the second day, Perry played a morning foursome with Furyk and they defeated Pádraig Harrington and Robert Karlsson (3 & 1). Also on day two, Perry played an afternoon fourball with Furyk and they lost to Ian Poulter and Graeme McDowell (1 up). On the third day, Perry played in a singles match and defeated Henrik Stenson (3 & 2). Team USA defeated Team Europe 16½ to 11½. Despite rumors that he would retire following Team USA's Ryder Cup victory, Perry confirmed at the start of the 2009 PGA Tour season that he hoped to win at least eight more tournaments, which would take his career total to 20. Twenty wins ensures a lifetime PGA Tour membership. Perry won his first event in 2009 in his third start at the FBR Open, where he defeated Charley Hoffman on the third playoff hole with a birdie. It was his 13th career tour win. He maintained a rich vein of form throughout the first few months of the 2009 season, making ten cuts in ten events and registering five top-10 finishes during this streak. In April 2009, Perry was the 54-hole co-leader at The Masters and held the lead by two strokes with two holes to go. However, he recorded two straight bogeys, after failing to find the green in regulation at both the 17th and 18th holes. This resulted in a sudden-death playoff with Ángel Cabrera and Chad Campbell. Perry made par on the first extra hole, to match Cabrera, but Campbell was eliminated after he made bogey. At the second extra hole, Perry missed the green from the middle of the fairway and then ran his pitch well past the hole, resulting in a bogey. Cabrera then won the playoff and the tournament with a par. Perry would have become the oldest winner of The Masters at 48 years old, 8 months, and 2 days. He received over 700 letters and emails in the aftermath of his playoff defeat, including a note from former President George W. Bush.  Perry won his second event of 2009 at the Travelers Championship in June, coming from one stroke behind Paul Goydos. Perry shot a final round 63 and won his 14th tour event, one win closer to his goal of 20 career wins. He won the event by three strokes over Goydos and fellow American David Toms. With the win he moved into a career high spot of four at the Official World Golf Ranking. Perry is among the winningest and highest all-time PGA Tour money winners without a major championship, with fourteen wins and career earnings of over $32 million.