In case you haven’t heard by now, Tiger Woods will take on Rory McIlroy, Jason Day and Hideki Matsuyama in Monday’s MGM Resorts The Challenge: Japan Skins. But while it’s a new competition created by GOLFTV, Tiger teeing it up in made-for-TV events is certainly something golf fans have gotten used to seeing since Woods turned pro in 1996. In fact, Woods previously has played in 23 of them—we’re counting events consisting of 36 holes or fewer with a maximum field of four players—a testament to his lengthy reign as the game’s biggest draw.
Yet while Woods has been the main attraction for many of these events, from the old Monday Night Golf series to “The Match” a year ago to this year’s Challenge, he hasn’t been the dominant force in them that one might expect. Overall, Woods has been on the winning side in 11 of his 23 appearances. And the craziest part is that that includes a ridiculous seven wins in eight starts at the PGA Grand Slam of Golf, in which he took on the three other major champs from that year (or, at least, three other quality players).
Woods’ results have been particularly disappointing (if you can even call silly-season events “disappointing”) in the former Skins Game, going winless in six attempts. Using that as a barometer, it’s not surprising that oddsmakers have McIlroy (2-to-1 odds) and Matsuyama (5/2) favored to win the most money over this year’s Masters champ (3/1) in the four-man field. But before we get to that competition, here’s a look back at all 23 of Tiger’s previous made-for-TV appearances, ranked.
23. 2001 Skins Game: Incredibly, Woods played in six Skins Games (1996, 1997, 2001, 2002, 2004 and 2005) and never won. But 2001 was the only time he got shut out in the former Thanksgiving weekend special. Not that he was alone that year as Greg Norman swept the entire $1 million purse against Tiger, Colin Montgomerie and Jesper Parnevik. You might remember this was the year you had to “validate” your skin. Don’t worry, that will NOT be the case in Japan this week.
22. 1996 Skins Game: Woods’ first Skins Game appearance yielded a slightly better return (two skins for $40,000), but won’t exactly be remembered in the same way as his “Hello, world” announcement a few months prior.
21: 1997 Skins Game: Even after winning the Masters by 12 shots, Woods could only muster three skins for $60,000. A trend was clearly developing. And not a good one.
20. “Battle at The Bridges” (2005): Part of the Monday Night Golf series that began with the “Showdown at Sherwood” in 1999, this was supposed to be a clash of the Big Four at the time, but Vijay Singh refused to play—possibly due to a confrontation with Phil Mickelson at that year’s Masters over Mickelson’s spikes. Instead, Tiger and Singh’s replacement, John Daly, lost to Mickelson and Retief Goosen, who wound up filling in for Ernie Els, 5 and 3. Maybe that’s why Woods was so determined to beat Daly in that epic playoff at Harding Park a few months later.
19: “The Match” (2018): On a Shadow Creek course set up for fireworks, Woods and Mickelson struggled to make birdies. Tiger provided the day’s biggest highlight (by far) with a birdie chip-in on 17 that squared the match, but lost in a playoff on a makeshift, 93-yard, lighted par 3 that Woods managed to miss three times. As a whole, the event also failed to deliver on a promise that it would be as much about entertainment with trash-talk and side bets as it would about the competition. The $9 million winner-take-all (wink, wink) purse was intriguing, but fans were relieved to get their money back after plunking down $19.99 on Pay-Per-View and getting refunded when Turner Sports had technical difficulties.
18. “Battle at The Bridges” (2003): Despite top-ranked Tiger teaming up with World No. 2 Ernie Els, the tandem lost to Mickelson and Sergio Garcia, 3 and 1. We’re guessing Woods won’t spend too much time on that in his upcoming memoir.
17. 2005 Skins Game: In Tiger’s final Skins Game appearance, he missed an eight-footer for birdie on 18 that gave Fred Funk six skins for $550,000 and $925,000 for the event. Woods won the other $75,000, but he had to be kicking himself for losing to a 49-year-old who had been outdriven by fellow competitor Annika Sorenstam earlier in the day.
16. 2002 Skins Game: Woods earned his biggest payday at the Skins Game to date ($125,000), but still got drubbed by his buddy Mark O’Meara and lost a final $200,000 skin to Mickelson. It’s also unclear how much Woods actually netted after his caddie, Steve Williams, threw a fan’s camera into a lake after believing his boss was distracted by its clicking on a bunker shot. “I think Tiger wound up paying for the camera,” Williams told Golf Digest in 2015.
15. “The Match at Mission Hills” (2013): For a second consecutive year, Tiger shot 68 in a one-on-one showdown with McIlroy in China. And for a second consecutive year, McIlroy shot 67 to win. “I would like to play all my tournaments in China where I can beat Tiger,” McIlroy joked after. He’ll see if he can keep that run against Tiger going in Asia this week.
14. “Duel at Lake Jinsha” (2012): As mentioned, Rory beat Tiger by the identical score in an exhibition the year before, which was the final official Monday Night Golf event. This one gets the edge over 2013 because Woods lipped out a bunker shot on final hole that would have tied the match. Also, using DUEL in the title is a bit spicier then match.
13. 2004 Skins Game: Woods’ closest call at the Skins Game ended with a tee shot into the water on the fourth playoff hole, the 204-yard, par-3 17th at La Quinta’s Trilogy Golf Club, which gave Fred Couples his record sixth win in the event. Still, Tiger took home $310,000, and at least he made Mr. Skins sweat for once. Well, in theory. Freddie doesn’t sweat over anything.
12. 1997 PGA Grand Slam of Golf: Making his first appearance in the event pitting the year’s four major champs, Tiger lost to U.S. Open winner Ernie Els by three shots. Woods would play in this event seven more times and never lose again. Incredible.
11. “Battle at Bighorn” (2000) Tiger played pretty well, but lost 1 up to Sergio Garcia. Knowing how their “rivalry” (really more a feud) turned out, this probably burns Tiger to this day. But kudos to Sergio. Not a lot of people can say they took down Tiger during that historic 2000 campaign. This also drew a ridiculous 7.6 rating.
10. “Battle at the Bridges” (2004): Tiger and Hank Kuehne (random!) beat Mickelson and Daly, 2 and 1. This did not do a ridiculous 7.6 rating.
9. “Battle at Bighorn” (2001): Monday Night Golf went with a mixed doubles foursomes format as Tiger and Sorenstam defeated David Duval and Karrie Webb on the first playoff hole. We’d put this higher, but it was Sorenstam and not Tiger who made a 10-foot birdie putt on final hole of regulation to keep the match going.
8. 2006 PGA Grand Slam of Golf: Tiger won his final appearance in this event, but only by two shots over Jim Furyk. A pretty weak effort by Woods at Poipu Bay by his lofty standards.
7. 1999 PGA Grand Slam of Golf: Woods defeated Davis Love III in the final in the second of two years this event used a match-play format.
6. 1998 PGA Grand Slam of Golf: Woods defeated Vijay Singh in the final in the first of two years this event used a match-play format. Yeah, these two are tossups.
5. 2000 PGA Grand Slam of Golf: Woods beat Vijay again, but this time in a playoff. Drama!
4. “Battle at Bighorn” (2002): Tiger teamed with Jack Nicklaus—talk about a dynamic duo!—to beat Garcia and Lee Trevino, 3 and 2. Woods made nine birdies in 16 holes. When you impress a guy with 18 majors, you’ve done well for yourself.
3. 2005 PGA Grand Slam of Golf: With scores of 67-64, Woods won by seven shots over Mickelson, who was returning to the event after his second-round 59 the previous year. Message received.
2. “Showdown at Sherwood” (1999): The OG of made-for-Tiger/made-for-TV events. What a title! What a matchup! Woods won this battle of the world’s top two players, 2 and 1, to collect a check for $1.1 million. And the 6.9 Nielsen rating topped every golf broadcast from the year other than the final round of the Masters. Monday Night Golf was a force to be reckoned with! At least, for a few years.
1. 2002 PGA Grand Slam of Golf: Woods shot a second-round 61 to win by 14 shots over Davis Love III and Justin Leonard. Not quite the 15-shot margin by which he won the 2000 U.S. Open at Pebble Beach, but keep in mind this was a 36-hole event. Even Tiger looks like he feels bad for destroying the field in this photo:
Kidding. He was probably ticked he didn’t win by 20.