The 7 funniest/most memorable moments in The Match history

the match best, most memorable moments

With the seventh edition of The Match starting on Saturday, let's take a look back at the best moments from the previous six.

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The newest edition of The Match tees off at 6 p.m. ET on Saturday on TNT, and this one boasts a star-studded cast of pro golfers: Tiger Woods, Rory McIlroy, Jordan Spieth and Justin Thomas.

These things are always well-publicized in the lead-up to the event, and this one’s been no different. That said, it should be one of the franchise’s better installments. Woods is back, playing for the third time and first since May 2020. He brings eyeballs alone, but the threesome he has joining him aren’t exactly slouches (it’s also Spieth’s debut). Plus, they are all pretty good at needling each other, an important part of gamesmanship that’s pivotal to these types of matches. Remember, this is golf, but we are watching for entertainment, right?

But before we turn the page to the seventh edition of The Match, let’s take a quick second and appreciate the six prior and the best, funniest, most rewatchable moments from them. Here’s hoping we’ll have more moments to add to this list after Saturday’s matchup.

Tom Brady’s debut

Tom Brady has a ton of MVP trophies but he also deserved one for his play in The Match: Champions for Charity at Medalist in May 2020. This was the rematch after Woods and Phil Mickelson faced off in the first, but this time they were joined by Brady (with Mickelson) and Peyton Manning (with Woods).

Brady wasn’t the best player this day, but he was the most entertaining. He played like a weekend hacker and was roasted on Twitter for it, ripped his pants, air-counted shots standing on greens and, then, hit the best shot of the day, holing out from the fairway.

Josh Allen’s golf ball

The Match VI was an all-quarterback showdown, and Buffalo Bills star Josh Allen put a unique golf ball in play: one with a shirtless Brady (from the NFL Combine) as the logo.

Brady, who played at Michigan, fired a quick jab back at Allen, who went to Reedley junior college before he played at Wyoming.

“Never heard of that [brand of golf ball],” Brady said. “You went to a college I never heard of and now are playing golf balls I never heard of.”

Sir Charles

Charles Barkley has been the star analyst for most of these. Here are some of his best lines from the matches.

“This is the longest I’ve been in Vegas without drinking in 30 years.”

“This is some crappy golf. Y’all know that?”

“I don’t like playing charity tournaments. … It’s very nerve-wracking because once you hit the first person, you get really nervous.”

“Everybody knows I like to gamble. I wanna be dead broke when I keel over. I don’t want to leave all that money for my free-loading family. I’ve been taking care of them my whole life. I wanna be dead broke at my last breath.”

“I need that lube. I need that liquid lube. I have a couple cigars and have me a couple alcoholic beverages. Listen, you can’t play golf and not drink. It’s the only sport they let you drink while you are playing it. There’s a reason why: it’s the most unbeatable game in the world.”

Free golf!

Remember that first edition of The Match, the one with Mickelson and Woods squaring off at Shadow Creek for a suitcase full of cash? It was supposed to be available only for those who paid for it, but there was a glitch. Website and streaming issues left viewers frustrated and unable to either pay for the access or watch it due to laggy streaming. Eventually, Turner just decided to stream The Match for free.

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More free golf!

But the bonus golf didn’t end there. Woods and Mickelson were all square in the inaugural Match, tied on the first playoff hole and then, due to darkness, converted the par-5 finishing hole into a bizarre, downhill 93-yard par-3 played under the lights. Mickelson eventually won with a birdie.

A home-course advantage

At The Match: Champions For Change in November 2020, Mickelson and Barkley took on Manning and Steph Curry at Stone Canyon Golf Club in Oro Valley, Ariz. On the 8th hole, Mickelson hit a drive way right that seemed it was certain to go O.B., but it hit off a rock and bounced back into play, just inches from the fairway. Driving to his ball, and broadcast team joked with Mickelson, asking how he knew to play it off the rock.

“I own the place,” Mickelson quipped. He did, literally.

Justin Thomas on the mic

If this golf thing doesn’t work out for Thomas, he was great as a guest on-course reporter for The Match II. Take our word for it.

Josh Berhow Editor

As’s managing editor, Berhow handles the day-to-day and long-term planning of one of the sport’s most-read news and service websites. He spends most of his days writing, editing, planning and wondering if he’ll ever break 80. Before joining in 2015, he worked at newspapers in Minnesota and Iowa. A graduate of Minnesota State University in Mankato, Minn., he resides in the Twin Cities with his wife and two kids. You can reach him at

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