As we prepare for Tiger vs. Phil, what other head-to-head matchups across the world of sports would we love to see?

By Daniel Rapaport
November 20, 2018

At the Players Championship in May, Phil Mickelson had this to say about his pairing with rival-turned-buddy Tiger Woods: “As I look at the cover of the newspaper and the pairing is on there and the excitement that’s been going on around here, it gets me thinking: Why don’t we just bypass all the ancillary stuff of a tournament and just go head-to-head and just have kind of a high-stake, winner-take-all match?”

With the benefit of hindsight, the intent of that statement is pretty clear—lay the foundation for a pay-per-view showdown against Woods. That foundation will come to fruition on Friday, when Tiger and Phil face off for $9 million in Las Vegas. But Phil’s suggestion of “skipping the ancillary stuff” and giving the people what they want is an intriguing one. It got us thinking—what other head-to-head matchups across the world of sports would we love to see?

Here are some mano-a-mano face-offs to consider, ranging from the farcical to the very possible. In the case of two guys being from completely different eras, imagine both in their primes.

Prime Tiger Woods vs. Prime Jack Nicklaus

The consensus two greatest golfers of all time missed each other’s prime by about 30 years. Tiger was at his best in the early mid-2000s while Jack owned the ‘70s. Everyone has their opinion as to who deserves the GOAT title, so what better way to settle it than a head-to-head matchup at Augusta National? To make things easier for Jack, we’ll allow him to use modern equipment rather than persimmon woods and a balata ball.

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Babe Ruth vs. Barry Bonds

It’s hard to appreciate Ruth’s greatness when the only videos we have of him are colorless and grainy as hell. We’d love to see how his power would stack up against that of prime Barry Bonds in a head-to-head home run derby. We’ll put this one at Yankee Stadium, where the short porch in right field would cater to both lefties.

Tony Romo vs. Stephen Curry

In golf, of course. These two can flat-out play; Curry has held his own in two Tour events, while Romo has been close to qualifying for the U.S. Open. This would help settle the debate as to who is the best non-golfing professional athlete at golf.

Garrett Ellwood/NBAE via Getty Images

LeBron James vs. Kevin Durant

These two have gone head-to-head in the last three NBA Finals, and every time one is guarding the other there is an added buzz. It’s the greatest player of his generation (and maybe ever) vs. the back-to-back Finals MVP. This would be an incredibly intriguing matchup—you’d have LeBron bullying KD physically and KD trying to out-finesse LBJ with his refined offensive game. Plus the potential for trash talk here is monumental. LeBron could zing KD for needing to join the Warriors to win a title, but KD can return the favor on ‘Bron for joining the Heat.

Roger Federer vs. Bjorn Borg

This one would have to be on Centre Court at the All England Club, because that’s the place both players have had the most success. Federer has won a record eight Wimbledon titles while Borg has won five. This would be one of the most aesthetically pleasing sporting events you’ll ever see—both men, dapper as can be, wearing all-whites on the most famous court in the sport, with dueling one-handed backhands. Sign me up.

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Serena Williams vs. Martina Navratilova

Sticking with tennis, this would be an all-time clash of styles. Serena does the majority of her damage from the baseline, where her powerful right-handed groundstrokes often overpower opponents. Navratilova, on the other hand, was a classic lefty serve-and-volleyer who won with guile and strategy. This one would also be at Wimbledon, where Serena has won nine times to Martina’s seven.

Muhammad Ali vs. Mike Tyson

Tyson didn’t have the longevity of some of the all-time great heavyweights, but he was as dominant as anyone at his best. Tyson was a ferocious puncher who came at you right from the first bell, often knocking his opponent out before he knew what hit him. He was also a fantastic trash talker, which makes this hypothetical fight particularly intriguing. Ali is perhaps the greatest trash talker of all time, regardless of the sport, and backed it up with his graceful style in the ring. Though some of Ali’s greatest fights came in far-off locations, it’s hard to go with anywhere but Las Vegas for this one.

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