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THOUSAND OAKS, CA – OCTOBER 25: Tiger Woods watches his tee shot on the 10th hole while Phil Mickelson gets ready to hit during the final round of the ZOZO Championship at Sherwood Country Club on October 25, 2020 in Thousand Oaks, California. (Photo by John McCoy/PGA TOUR via Getty Images)

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THOUSAND OAKS, CA – OCTOBER 25: Tiger Woods watches his tee shot on the 10th hole while Phil Mickelson gets ready to hit during the final round of the ZOZO Championship at Sherwood Country Club on October 25, 2020 in Thousand Oaks, California. (Photo by John McCoy/PGA TOUR via Getty Images)
Phil Mickelson is famed in the golf world for his gambling habits and many engaging tales. However, it seems like they never end, do they? Every time we go on the hunt, a new one surfaces up. However, the most recent find is one of the most interesting, and it takes us back to when we witnessed the legendary showdown between Tiger Woods and Mickelson.
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The two of the greatest battled it out in the first iteration of ‘The Match’. Played in 2018, Phil emerged victorious after a lengthy battle of 22 holes, including four playoff holes. He took home a massive sum of $9 million amongst the chance of a lifetime of boasting his win over the greatest ever.

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AKRON, OH – AUGUST 01: Phil Mickelson (L) and Tiger Woods smile during a practice round prior to the World Golf Championships-Bridgestone Invitational at Firestone Country Club South Course on August 1, 2018 in Akron, Ohio. (Photo by Sam Greenwood/Getty Images)
Moreover, his affable and vocal personality spares no one when he reigns supreme. A similar situation played out back in 1998 when the two were gambling on course. Let’s take a look at it-
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Phil Mickelson and Tiger Woods’ first gamble
The story about the first time Lefty and Woods clashed with each other on the course was first told by Doug Ferguson of the Associated Press. Later, ESPN’s Shane Ryan relayed the story about their face-off in the 1998 Nissan Open.
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Mickelson won ‘big’. After this, however, came something we can only expect from Mickelson. He stuck photocopies of Tiger’s $100 notes in his locker, along with a hilarious note addressed to him. It read, “Just wanted you to know Benji and his friends are very happy in their new home.”

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OWINGS MILLS, MARYLAND – AUGUST 26: Phil Mickelson of the United States walks on the first hole during the first round of the BMW Championship at Caves Valley Golf Club on August 26, 2021 in Owings Mills, Maryland. (Photo by Tim Nwachukwu/Getty Images)
This, however, is just one example of Mickelson’s notoriety for gambling in the golf world. From losing a $1 to a patron at the Augusta Masters (which he had to borrow from a caddy), to hitting a shot over a pine tree for $1,200, he’s done it all.
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Which story is your favorite though?
Read More- ‘Complimented or Insulted’: Golf World Reacts to Tiger Woods’ Bizarre Assessment of Collin Morikawa
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