The Tiger Woods rivalry with lesser-known golfers has shaped some of the most unforgettable moments in modern golf, challenging Woods in fiercely competitive showdowns and pushing him to new heights. While big names like Phil Mickelson and Vijay Singh often stole headlines, it was underdogs such as Bob May and Rocco Mediate who tested Woods in ways his most famous adversaries could not, especially during high-stakes tournaments like the PGA Championship.
How Rivalries With Major Golf Stars Played Out
Phil Mickelson’s career has always been intertwined with that of Tiger Woods, with their on-course battles capturing global attention. Mickelson himself once said,
“He brought out the best in me and forced me to work harder and focus to ultimately achieve the success that I’ve had.”
—Phil Mickelson, Professional Golfer. Fellow top-tier golfer Vijay Singh also found motivation in facing Woods, aiming to surpass the 15-time major winner. However, according to insiders, playing regularly with Woods made it harder for these established stars to surprise him, as their styles became familiar and predictable to the golf icon.
Steve Williams, a long-time caddie for Woods, shared insights on the dynamics of these rivalries.
“Guys like Phil and Vijay, they were playing with Tiger week in and week out, and they were frequently paired with him. 9 times out of 10, when they were paired with Tiger, he got the better of them on the score that was posted on that day,”
—Steve Williams, Former Caddie. This routine pairing put added pressure on the likes of Mickelson and Singh, as Woods became adept at handling their strengths and tactics.
Why Lesser-Known Golfers Created Unexpected Obstacles
Williams explained that the real challenge for Woods came not from familiar faces but from competitors he rarely played against.
“When you get an unheralded guy that’s not played with Tiger a lot and he’s playing with him in the final round of a major championship, everybody’s thinking Tiger’s going to win the tournament. There’s a lot of pressure, we know that. But these guys are under no pressure because they’re not expected to win, and they rise to the occasion,”
—Steve Williams, Former Caddie. Without the weight of expectation, golfers such as Bob May, Rocco Mediate, and Chris DiMarco could play freely, occasionally presenting Woods with unexpected resistance in critical matches.
Statistics support this perspective, as top contenders like Mickelson, Singh, and Ernie Els, despite their world-class play, rarely bested Woods in direct competition. Ernie Els, for instance, found himself frequently coming up short against Tiger in key tournament moments. As Williams noted,
“Ernie Els was an absolutely wonderful player. But he hardly ever got the better of Tiger. Sometimes, when you play with somebody on a regular basis and someone keeps getting the better of you, you almost know that the guy is going to get the better of you,”
—Steve Williams, Former Caddie.
Bob May’s Legendary Duel With Woods at Valhalla
The 2000 PGA Championship at Valhalla Golf Club became the ultimate showcase of this theory in action. In the opening rounds, Woods shared the spotlight with legends such as Jack Nicklaus and Vijay Singh, seizing an early lead. However, Bob May, a relatively unheralded golfer, emerged as Woods’ fiercest challenger, particularly after posting an impressive third-round 66 to draw just one stroke behind entering the final day.
The championship’s final round delivered dramatic twists, as May surged ahead early before Woods caught up with crucial play in the closing holes. As fatigue and pressure mounted, their scores matched at the end of regulation, forcing a gripping three-hole playoff. Woods began the playoff by birdieing the 16th, then held steady with pars on the closing two holes, narrowly overcoming May’s upset bid. According to Williams,
“In all the major championships that Tiger played, in the time that I was with him, Bob May tested Tiger better than anyone. Tiger expected that from him because I’d never heard of Bob May, and Tiger told me when this guy was a junior in Southern California, he was the man!”
—Steve Williams, Former Caddie. The intensity of this showdown was a defining testament to how unexpected opponents could draw out an entirely new level of performance from even the greatest golfer of his generation.
Why The Lesser-Known Challengers Stand Out
Unlike familiar foes who struggled under the pressure of expectation, Bob May, Rocco Mediate, and similar underdogs entered matches against Woods without the psychological baggage of repeated defeat. During Woods’ dominant era—marked by record-setting achievements like his 1997 Masters victory at Augusta National Golf Club and his string of major wins in 2000—these lesser-heralded challengers turned potential disadvantages into opportunities. Their open-mindedness, coupled with lower external expectations, enabled them to play some of their best golf precisely when most eyes were on Woods.
For Tiger Woods, these surprise opponents provided some of the most heart-pounding and unpredictable contests of his legendary career. Facing relatively unknown players on the biggest stages forced him to stay vigilant and adapt to new threats, making the Tiger Woods rivalry with lesser-known golfers a crucial part of his legacy. As history shows, it wasn’t always marquee names like Phil Mickelson or Ernie Els who pushed Woods to his absolute limits, but often unsung talents determined to seize their moment.
The Enduring Impact of Tiger’s Rivalries
The most intense challenges for Tiger Woods often came from golf’s underdogs, rather than the fellow superstars he faced most frequently. The drama of the 2000 PGA Championship and similar matchups not only tested Woods’ resilience, but also elevated the stature of players like Bob May in the eyes of fans and historians. Looking ahead, these lesser-known rivalries continue to inspire new competitors, proving that anyone—no matter their past accolades—can rise to the occasion when matched against one of golf’s greatest icons.