“He brought out the best in me and forced me to work harder and focus to ultimately achieve the success that I’ve had.” This is what Phil Mickelson had to say about his rivalry with Tiger Woods back in 2018. Despite the constant back-and-forth they had on and off the course, Phil respected everything his adversary did with his club. Even Vijay Singh wasn’t intimidated by Woods, but rather wanted to beat him, bringing out the best in himself. You’ll be surprised to know that although it was Tiger bringing out the best in Vijay Singh and Phil Mickelson, it wasn’t the same for Woods.

Former long-time caddie Steve Williams joined the crew of Golf’s Subpar Podcast recently. During one of the segments, host Colt Knost requested their guest’s opinion about how guys like Bob May and Rocco Mediate were able to push Woods more than Mickelson and Vijay Singh. “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,” said the ex-caddie.

Knowing how Mickelson and Singh played gave Woods the advantage against them as he got used to their play, according to Williams. Nothing they did surprised him anymore. Hence, it was much easier for Woods to play against them than against other lesser-known names. As Steve elaborated, “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.”

Considering their respective records against Tiger Woods, Phil Mickelson and Vijay Singh were always under pressure to perform. Especially since they were considered players who had the potential to outshine the 82-time PGA Tour winner. However, the likes of May, Mediate, and Chris DiMarco had no pressure on them when they faced Woods. With all eyes on Tiger, these less prominent stars had the opportunity to slide under the radar and focus on performing better themselves.

Steve then added, “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.” Els, despite being in the prime of his career, struggled to tackle the challenge of Woods. Especially in 2000, when Tiger won three majors, two of them had the South African in the runner-up position. After a point, Els knew that Woods had an advantage against him. But for Bob May, that was not the case.

“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!” Seems like Woods was prepared for the challenge he would face from May. Yet, things went down to the wire at the 2000 PGA Championship. The pair battled it out outside the regulation holes at Valhalla, and Woods barely scraped through with a win in the three-hole playoff.

That day at Valhalla Golf Club can still be considered one of the most exciting and nail-biting days of golf. But how did things turn out the way they did?

Bob May pushed Tiger Woods to his limits

The first couple of days of the 2000 PGA Championship were a treat for the fans. The Valhalla Golf Club had paired up Tiger Woods with Jack Nicklaus and Vijay Singh. It was also Nicklaus’s last PGA Championship appearance, which made the moment extra special. The Golden Bear got to witness Woods in action as the latter shot 66-67 to take a 1 stroke lead after 36 holes. However, a 2-under 70 in the third round put his lead under threat after Bob May shot a 66 on Saturday to finish 1 stroke shy after 54 holes.

In the final round, Woods and May went head-to-head throughout the day. Two bogeys within the first 6 holes pushed the former back by 2 strokes while the latter managed 2 birdies and a bogey to go 2 strokes up. By the 14th hole, Woods was at -16 while May was at -17 as they managed 2 consecutive pars before things turned around. The 15-time major winner scored 1-under on the 17th and 18th to match Bob’s 18th hole birdie. That pushed things to a three-hole playoff on the 16th, 17th, and 18th holes. Tiger Woods got an early advantage with a 16th hole birdie and made par in the remaining holes to beat Boby May and lift the Wanamaker Trophy. During his prime, Phil Mickelson never troubled his rival this much.