From Tiger Woods to Tom Brady, a look at The Match’s top moments

Celebrating its three-year anniversary back where it all started, “The Match” is set for its fifth edition, a one-on-one showdown between Bryson DeChambeau and Brooks Koepka in Las Vegas.

The festivities have already begun, with DeChambeau hitting Koepka’s face from a tee box atop the Wynn Las Vegas. The two will settle their beef with a 12-hole match at the Wynn Golf Club on Nov. 26, the day after Thanksgiving, at 4 p.m. Eastern.

The series started with a showdown between two players with a combined 21 majors – Tiger Woods and Phil Mickelson. It also has showcased the winners of 10 Super Bowl titles (Tom Brady, Peyton Manning and Aaron Rodgers) and three NBA championships (all belonging to Stephen Curry -- sorry, Charles Barkley). The previous four editions of “The Match” have produced many memorable moments. As an appetizer for this latest event, here are the five best moments in the history of “The Match.”

Tiger and Phil play into the dark

Under the lights in Las Vegas, Woods and Mickelson added another chapter to their storied rivalry with their highly-anticipated, mano-a-mano showdown in the debut of “The Match.”

Neither player held a lead greater than 1-up in regulation. They walked off 18 all square, forcing the competition to extra holes. They both parred the 19th hole -- a re-playing of the par-5 18th -- before shifting to a custom, 93-yard 20th hole with a tee box on the Shadow Creek putting green.

Woods got up-and-down for par, while Mickelson just missed a birdie try inside 18 feet. Playing the hole again for the third playoff hole and 21st of the day, Mickelson again had a birdie putt for the win, but missed from roughly 6 feet away. Meanwhile, Woods had a 5-footer for par, which Mickelson told Woods to pick up, saying, “I don’t want to win that way.”

On the 22nd hole, with the lights now a necessity, Woods put his tee shot inside 10 feet, but Mickelson stuck his shot inside 5 feet. Woods missed his putt, Mickelson made his and collected the $9 million prize.

Tiger trolls Phil’s U.S. Open woes

“The Match II” featured Woods and Manning against Mickelson and Brady. The fifth hole featured a one-club challenge, requiring each player to use just a single club on the hole. Woods went with a 4-iron and Mickelson picked a 6-iron. Despite using a longer club, Woods had to hit his approach shot first.

As Mickelson prepared to hit his shot from a muddy lie some 150 yards away, he asked Woods to mark his ball on the green.

“You want me to mark it with my U.S. Open medal?” Woods asked, scoring a clear jab.

Responded Mickelson: “Do you have any? I got some silver ones. Do you have any other gold ones?”

“I should have three,” Tiger quipped back.

Credit Mickelson for taking this burn in stride. While his career has seen him win 45 PGA TOUR titles (tied for eighth all-time) and six majors, the U.S. Open is the lone title standing between him and the career Grand Slam. Mickelson has six runner-up finishes at his national championship, including a runner-up finish to Woods in 2002.

Tom Brady holes out, silences Barkley

One of the most poised and clutch athletes of all time, Tom Brady finally looked human when he made his debut on “The Match.” It got so bad that some even felt pity for Brady, who kept spraying shots out of bounds and into trouble. Brady’s struggles allowed Woods and Manning to take a 3-up lead over Mickelson and Brady.

It got to the point where celebrities were calling in to try to incentivize Brady to turn things around. Koepka offered to donate $100,000 to charity if Brady could muster a par on the front nine. Barkley offered $50,000 if Brady could hit the green on the par-3 fourth hole. Brady was flailing.

But then came the par-5 seventh hole. Brady was 130 yards from the hole after three shots.

“How many shots you want?” Barkley teased Brady as he walked up to his ball. “Aw, come on, I’m going to give you some shots man, I want some of you.”

“Don’t worry, it ain’t over yet,” Brady responded.

Brady proceeded to hit a high, arching approach shot that took a bounce behind the hole and spun back into the cup.

“Shut your mouth, Chuck,” Brady celebrated. “Take a little of that medicine. Get your butt out here.”

It was pinpoint accuracy by the winningest quarterback of all time.

Brady’s celebration only lasted briefly (pun intended). As he bent down to pull his ball out of the hole, he split his pants.

Can’t this guy catch a break!?! The hole-out birdie sparked a run by Mickelson and Brady that pushed “The Match: Champions for Charity” all the way to the final hole. Woods and Manning hung on to win, 1 up, however.

Barkley uses ugliest ball in golf history

Charles Barkley got out of the broadcast booth for his debut in the third edition of “The Match.” This one featured Barkley and Mickelson against Manning and Curry. Barkley, known for his awful swing and love for the game, wowed fans with clear improvements to his action. A confident Barkley even picked up his tee on No. 1 before his ball landed in the fairway.

But the most memorable moment of the match came when Barkley’s “NBA on TNT” mates, Ernie Johnson, Kenny Smith and Shaquille O’Neal, joined the broadcast. As they started to mock Barkley, Mickelson pulled out a ball with Shaq’s face on it.

“This the ugliest ball in the world,” Barkley said before taking a whack at it.

However, Barkley’s surprisingly solid play helped lift the underdog team to victory, as Mickelson and Barkley beat Manning and Curry, 4 and 3, the widest margin of victory in “The Match” history.

Bryson’s Montana mountain shot

The Reserve at Moonlight Basin offered the mighty DeChambeau a new challenge: With all the elements in his favor, just how far could he hit it? Pretty far, as it turned out.

Teeing off from the elevated eighth tee on the Madison Range of the Rocky Mountains, DeChambeau stared down the 777-yard hole and hit his drive 480. The shot, which was helped by a steep downslope, was epic, but he was still disappointed to have narrowly missed the 500-yard mark.

“Some would find that inspiring and as I walk off, I just feel defeated,” Mickelson said in awe.

DeChambeau hit a mulligan to try to reach 500 yards, but pulled it left.

Aaron Rodgers, his partner, hit the second-farthest tee shot in the group, reaching 438 yards. Mickelson pulled up at 390 yards and Tom Brady mustered a drive of just over 300 yards. Those four tee shots were worth a donation of 1.7 million meals to Feeding America.

While the eighth hole was a nice show, DeChambeau and Rodgers won the match on and around the greens. DeChambeau chipped in for birdie on No. 1 and Rodgers walked in multiple putts, Kevin Na-style, for the win.