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By Josh Sens
Thursday, July 05, 2018

In their long, celebrated, overlapping careers, Tiger Woods and Phil Mickelson have been many things to each other: rivals, teammates, practice round confidants, comic foils. And now comes word that they're aiming to take on the roles of co-stars in a $10 million made-for-TV challenge match. As we look ahead to what would be a blockbuster two-man event, let us also look back at the two men and their shared history. From an ample list of candidates, we've selected the 18 most memorable Phil-and-Tiger moments.

1. THE WAY THEY WERE

Phil and Tiger have been grouped together 37 times on the PGA Tour. In those mano-a-mano matchups, Woods holds the slight edge, 18-15-4. Their first head-to-head was at the 1997 NEC World Series of Golf, and it was close. Very close. They both shot 72. In their latest meetings, at the Players in May, Woods topped Mickelson in each of the opening rounds (72-79 Thursday; 71-73 Friday).

2. TRADING PLACES

Rivalry? In its early years, it was more like the relationship between a hammer and a nail, with Tiger pounding Phil in 10 of their first 18 head-to-head meetings. Woods, meanwhile, won eight majors before Mickelson nabbed his first. But time has worn kindly on Mickelson, who has won all five of his majors since turning 33. By that age, Tiger had 14 majors in his bag. He's since been more successful collecting surgeries.

3. MASTER OF NONE

The final round of the 2001 Masters couldn't have felt especially good for Phil. Earlier in the week, he'd admitted to "desperately" wanting to win the event. And by Sunday there he was, paired with Tiger in the final group, just one shot back. But the round played out the way so many rounds did in the early days of their rivalry. Woods shot a steely 68 to Lefty's lukewarm 70. By day's end, the still-majorless Mickelson bore first-hand witness as his nemesis completed the Tiger Slam.

4. PARDON THE INTERRUPTION

Tiger got the props. But Phil got the laughs just prior to their start at the 2002 Tour Championship at East Lake, where the two were paired in the opening round. The punchline was set up by the starter, who introduced Woods on the first tee by listing some of his notable achievements. The list went on. And on. And on. Until Mickelson broke in with an "Alright, alright," his playful way of saying, "Enough already!" His timing and delivery were impeccable. Tiger joined the crowd in busting up.

5. INFERIORITY COMPLEX?

In 2003, an on-course rivalry crossed into new terrain when Phil, speaking freely in a GOLF interview, took to talking about Tiger's clubs, asserting that Woods was playing "inferior equipment." The full quote went like this: "In my mind, Tiger and I don't have issues between us. Well, maybe one. He hates that I can fly it past him now. He has a faster swing speed than I do, but he has inferior equipment. Tiger is the only player who is good enough to overcome the equipment he's stuck with." It sounded like a compliment, wrapped in criticism. Or was it the other way around?

6. A PHIL-AND-TIGER FLOP

At the 2004 Ryder Cup at Oakland Hills, U.S. captain Hal Sutton paired Woods and Mickelson for the first time, insisting that the two would be "as strong as new rope." Frayed not. Looking sullen in each other's company, the un-dynamic duo lost 2 and 1 to Colin Montgomerie and Padraig Harrington in Friday morning's four-ball session, then fell in afternoon foursomes to Darren Clarke and Lee Westwood, who bested Phil and Tiger 1 up.

Woods and Mickelson teamed up at Oakland Hills, but the stars didn't have their best stuff.

TIMOTHY A. CLARY/AFP/Getty Images

7. TABLING ANY ISSUES

Though their 2004 Ryder Cup pairing proved to be a clunker, the two have played nicely as teammates in a number of Ryder Cups and President Cups — at the Ping Pong table. Their paddle-battles have helped foster broader locker room camaraderie. If that doesn't warm you heart, consider this: When Woods's daughter, Sam, was born, Mickelson bought her a mini Ping Pong table as a gift.

8. SHOOTOUT AT DORAL

Although they've played together on more prestigious stages, one of Phil and Tiger's most riveting head-to-heads came in the final round of the 2005 Ford Championship at Doral. To call the contest a birdie-fest does not do justice to the drama of the day, with the two men dropping bombs on each other down the stretch. The crowd was going ballistic. Woods shot 66 to win by one on a stage where the acoustics were cranked up to 11. "What a day!" Woods said afterward. "If you're not nervous on a day like this, you're not alive."

9. TRY THIS ON FOR SIZE

When it comes to closing ceremonies at the Masters, you can bet that Tiger would rather don the green jacket than help another player slip one on. But in 2006, when Phil won his second Masters, Tiger put on a happy face while doing his sartorial duties as defending champ. Turn about is fair play, after all. Only a year before, Mickelson had done the same for him.

When Woods won the 2005 Masters, it was Phil Mickelson who dressed him with the jacket. A year later Tiger returned the favor.

John Biever

10. IN PERFECT HARMON-Y

To many Tiger-and-Phil-ologists, a watershed moment came in 2007, when Mickelson enlisted the swing-guru assistance of Tiger's former coach, Butch Harmon. The move paid immediate dividends, as Phil won his first Players Championship that spring.

11. THE BATTLE OF WOUNDED KNEE

Torrey Pines was a childhood training ground for both Phil and Tiger. In 2008, they played the familiar turf together in the first two rounds of the U.S. Open. Phil went out with 71-75 and finished T18. Tiger, you might recall, didn't sprint to victory. He limped to it, beating Rocco Mediate in a Monday playoff while playing with a stress fracture in his left leg and a torn ligament in his left knee.

12. AN ATMOSPHERE UNLIKE ANY OTHER

The Sunday roars were in full-throat at the 2009 Masters, as the two men, playing together, treated patrons to a dazzling display of pyrotechnics. Phil made six birdies. Tiger dropped an eagle on the 8th. Both players flat-lined on the back nine, but if you're keeping score (and you KNOW they were), Mickelson edged Woods, 67-68.

13. NO MAJORS, BUT STILL A WIN-WIN

The 2009 season came and went without a major title for Phil or Tiger. But neither man deserved much sympathy. Mickelson claimed his first World Golf Championship at Doral and bested Woods by three shots at the Tour Championship. Tiger, for his part, closed the year with six wins and captured his second FedEx crown.

14. A PHIL-GOOD STORY

Always at the center of attention, Woods was even more a media magnet at the 2010 Masters, which marked his return to competition after the scandal. Soon enough, though, Mickelson stole the spotlight by snagging his third green jacket. Tiger finished T4.

15. A GOOD ROUTING

Sunday at the 2012 AT&T Pebble Beach National Pro-Am found Woods and Mickelson in the final group, and it was Mickelson's turn to administer a whooping. How thorough was the pummeling? Lefty posted a 64 to win while whomping Tiger by 11 shots.

Phil got the best of Tiger during the final round of the AT&T Pebble Beach National Pro-Am.

Getty Images

16. I LOVE YOU, MAN

Could this be a "burgeoning bromance?" a reporter asked early in the week at this year's Masters. It seemed a reasonable question after a Tuesday morning that unfolded like a classy Judd Apatow script. Despite competing in a combined 45 Masters, Phil and Tiger had never played a practice round together at Augusta. So this was a first, and what a first it was, with Woods and Mickelson teaming up in a nine-hole match against Fred Couples and Thomas Pieters. The result was a smile-and-fist-bump-filled shotmaking demonstration that doubled as an old-fashioned shellacking, with Couples and Pieters on the losing end.

17. HEALING WORDS

Though it fell shy of being the stuff of a Hallmark card, by Phil-and-Tiger standards, it was pretty warm-and-fuzzy. It came in advance of this year's Players Championship, when Woods described what almost sounded like a … friendship? "Our relationship has certainly gotten a lot closer," he said. "When I was trying to deal with nerve in my back, trying to come back and trying to play and I wasn't very good, he always texted me some very encouraging words."

18. DON KING, EAT YOUR HEART OUT

Grouped in the same three-ball for the first two rounds of this year's Players Championship, neither Phil nor Tiger had his A-game. But their press conference performances were pure money, with each man taking cheeky jabs that ring, in retrospect, like promotional hype. "Why don't we just bypass all the ancillary stuff of a tournament and just go head to head and have kind of a high-stakes, winner-take-all match?" Mickelson asked Woods: "I'm definitely not against that. We'll play for whatever makes him uncomfortable."

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