The Skins Game has always thrived on star power and swagger, dating back to its 1983 debut with Nicklaus, Palmer, Player, and Watson trading cash, shots, and sharp trash talk as Player claimed the first $170,000 pot. Decades later, Annika Sorenstam, with 72 LPGA wins and 10 majors, shattered boundaries and stole the spotlight with a moment so bold it made a PGA Tour pro wear a skirt. 

With the Skins Game officially returning, there’s no better setup for the top three moments ever. Annika’s playful power move wasn’t just a viral clip; it captured exactly what made the Skins Game unlike anything else in golf.

It was the 2005 Merrill Lynch Skins Game, and Fred Funk lost a bet to Annika Sorenstam at the 3rd Par 5 at 535 yards. Funk shot at 271 from the tee, and Annika shot at 278. A PGA Tour pro was forced to play a hole wearing a skirt.

It was funny, sharp, and symbolic: a woman who once had to prove she belonged now setting the terms. The clip, posted by Skratch Golf, remains a reminder of her cultural impact and the Skins Game’s joyful chaos. 

It was more of the sporting moment of Funk that he wore the skirt happily and even made a shot while wearing it. However, Annika Sorenstam winning the bet is just one of the three memorable moments.

The Other Two Skins Game Moments That Made the Top 3

One of the most unforgettable Skins Game moments came when Chi Chi Rodriguez turned a simple question about wind direction into pure showmanship. Standing over his shot, he casually asked Arnold Palmer: “Arnie, how’s the wind blowing on this hole?” and then delivered the punchline by pretending to toss money into the air to see which way it fluttered. The crowd cracked up, Arnie grinned, and the entire exchange captured the Skins Game’s magic: legends competing for cash but never taking themselves too seriously. Finally, we come to the third moment.

The 2002 Skins Game delivered pure theater, with Mark O’Meara outdueling a powerhouse trio of Tiger Woods, Phil Mickelson, and Fred Couples on a day packed with near-misses and momentum swings. 

Tiger narrowly missed Hole 3, and O’Meara jumped in to claim two halves worth $75,000. Woods took Hole 5 for $50,000, while Couples saw his chance at Hole 8 lip out in brutal fashion. The momentum flipped for good when O’Meara won Hole 15 for $210,000, with Mickelson later taking $200,000 on 18 but still not enough. When the dust settled, O’Meara finished with $405,000, stunning three giants and showcasing exactly how quickly fortunes swing in the Skins Game. 

Now set to return after 17 years, the fans are hoping for more moments just like these, spontaneous, competitive, and unforgettable. If the revival captures even a fraction of this energy, golf is about to get back one of its most entertaining traditions. So, tell us which moment would rank on top?

Written by

Dolly Bhamrick

Edited by

Sagnik Bagchi