Made 18 of 22 cuts on the PGA TOUR, but finished 145th on the money list in 2009 with one top-10 of 2009, a T9 at the Legends Reno-Tahoe Open where he used a putter borrowed from Matt Bettencourt. In 2008, posted two top-10 finishes. Surpassed $1 million in earnings for the sixth time in his career. In a bid to become the oldest U.S. Open champion at age 45, lost in a playoff to Tiger Woods at Torrey Pines GC in La Jolla, CA. Finished regulation at 1-under-par 283 and held the clubhouse lead as Woods and Lee Westwood, both one stroke back, played the par-5 18th hole. Woods made birdie to force an 18-hole playoff. In the Monday playoff, made three consecutive back-nine birdies to take a one-stroke lead to the last hole. Woods made birdie to tie and force sudden death as both players shot even-par 71s. Woods parred the par-4 seventh hole, the first sudden-death hole, as Mediate made bogey after driving into a fairway bunker and missing a 20-foot par putt. In 2007, had best season since 2003, with a runner-up finish, three top-10s and more than $1 million in earnings while playing on a Minor Medical Extension. Spent early part of season as a walking commentator for GOLF CHANNEL. Led by three strokes through 36 holes of the Arnold Palmer Invitational after opening 66-65. Rebounded from third-round 76 with a 67 to finish solo second, his best finish since he was runner-up at the 2003 Deutsche Bank Championship-a span of 74 events. In 2006, was limited to 18 events as he battled long-time back injury. In contention at the Masters Tournament, as he sat T4 through 54 holes. Back problem flared up in final round, when he posted an 8-over-par 80 to finish T36. Not able to play for one month. Playing on one-time exemption as top-50 all-time money winner in 2005, rebounded from subpar 2004 season to finish in the top 125. Rallied down the stretch, with 12 made cuts in final 14 starts. Recorded lone top-10 of the season at the U.S. Open (T6). In 2004, finished outside the 125 on the TOUR money list for the fourth time in his 19-year career and for the first time since he finished No. 155 in 1995. In 2003, finished 31st on money list and was bounced from the field for season-ending TOUR Championship after missing cut in final full-field event, the Chrysler Championship. Began season with two top-fives in first three events, highlighted by a T2 at Mercedes Championships and a solo second at the inaugural Deutsche Bank Championship. In 2002, earned more than $2 million for the first time in his career and had best finish on the money list (22) since finishing 16th in 1993. Picked up first victory since the 2000 Buick Open with win at the Greater Greensboro Chrysler Classic. Had two-stroke lead over Mark Calcavecchia through 54 holes. Final-round 71 gained a three-stroke win over Calcavecchia and earned a career-high $684,000 paycheck. In 2000, earned his fourth career victory the way he won his first TOUR title-with a birdie on the final hole at the Buick Open. It was the first time he had led the Buick Open all week. Birdied two of final three holes for one-stroke victory over 54-hole leader Chris Perry. Victory lifted him over $1-million mark in a single season for first time in his career. In 1999, made clear comeback from 1994 back surgery with victory at the Phoenix Open in only his second start of the season. Held season-best 54-hole lead of six strokes. Final-round 71 earned him two-stroke victory over Justin Leonard. In 1997, made eight consecutive cuts near end of the year to retain full exempt status. Returned to TOUR in 1996 under special medical extension and tied for sixth at Phoenix Open to earn full playing privileges. Missed most of 1994 season with ruptured disk, for which he underwent surgery in July. In 1993, second TOUR win came in playoff at Kmart GGO, where he birdied fourth playoff hole to defeat Steve Elkington. Earned first TOUR title in 1991 in sixth season at Doral-Ryder Open. Sank 10-foot birdie putts on 71st and 72nd holes, forcing playoff with Curtis Strange. In Monday playoff, birdied first extra hole from 5 feet. Gained interest in golf in high school after years of playing baseball. With help from Champions Tour member Jim Ferree during college, began to construct his swing. At Florida Southern, coach Charlie Matlock became large influence on his game. Started using long putter to save his back and became the first player to win on TOUR using a long putter when he won the 1991 Doral-Ryder Open. Finished 600th out of 5,619 players in his first appearance at the 2005 World Series of Poker's Main Event. Began playing poker in 2004.