His best major finishes are playoff losses at the 1996 PGA Championship and 2009 Masters Tournament. For his success in leading the USA to victory in the Ryder Cup, he and fellow Kentuckian J. B. Holmes were named Kentuckians of the Year for 2008 by Kentucky Monthly magazine. He is good friends with former World Number 1 player Vijay Singh, who calls him "Biggie". Perry began playing on the Champions Tour after turning 50 in August 2010 while continuing to play on the PGA Tour. He won his first event in October 2011 at the SAS Championship. He nearly withdrew from the event after learning of his sister's death. In 2011, Perry split his time between the PGA Tour and the Champions Tour. He finished 15th on the Champions Tour money list playing in ten events. Although his focus was on the Champions Tour, he also had status on the PGA Tour until 2014 due to multiple wins in 2008 and 2009. Perry won for the second time on the Champions Tour early in 2012 at the ACE Group Classic. He shot rounds of 64 and 62 on the first two days to break the 36 hole scoring record on the Champions Tour and after ending with a 2 under par round of 70, he tied the overall tournament scoring record at 20 under par.  Perry was given a special invitation from the PGA of America to compete in the 2014 PGA Championship, held in his home state of Kentucky and site of his 1996 playoff loss; he finished T27. In 2015, he used a one-time exemption for being the top 25 of the career money list. He said he intended to play 18 events on the PGA Tour and only about seven on the Champions Tour, mainly the major tournaments. In 1993, Perry was inducted into the Kentucky Golf Hall of Fame. In 1994, he was inducted in the Western Kentucky University Hall of Fame. He was named the winner of the 2002 Charles Bartlett Award, given to a professional golfer for his unselfish contributions to the betterment of society, by the Golf Writers Association of America. In 2007, Perry was inducted into the Western Kentucky University Hall of Distinguished Alumni. On October 14, 2008, Perry was inducted into Lipscomb University's Athletics Hall of Fame. He won the 2009 Payne Stewart Award. On November 3, 2013, Perry clinched the 2013 Charles Schwab Cup. He was also named 2013 Champions Tour Player of the Year. PGA Tour playoff record (3–3)  CUT = missed the half-way cut "T" = tied WD = Withdrew   CUT = missed the halfway cut WD = withdrew "T" indicates a tie for a place  1Cancelled due to 9/11 QF, R16, R32, R64 = Round in which player lost in match play "T" = Tied NT = No tournament Note that the HSBC Champions did not become a WGC event until 2009.