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A week after Rory McIlroy, Dustin Johnson, Rickie Fowler and Matthew Wolff participated in the TaylorMade Driving Relief Skins Game, the world will get another opportunity to see four more professionals hit the links on May 24. However, not all four happen to be professionals in golf. The Match II will once again feature reigning Champion Phil Mickelson and the challenger Tiger Woods; however, this time around, each will be paired with a Hall of Fame QB as their partner. Mickelson will be joined by current Tampa Bay Buccaneers pivot Tom Brady, while Woods will form a duo with five-time NFL MVP Peyton Manning.

Woods/Manning (-225) | Mickelson/Brady (+175)

It probably shouldn’t be all that surprising that Team Tiger is the overwhelming favorite a week away from The Match II. As the old saying goes, you’re only as strong as your weakest link, and it would appear that Manning is the superior golfer to Brady. At least that’s what the limited data we have would suggest. It might have something to do with the fact that Manning’s had a little more time on his hands the past half-decade, but the former first-overall pick in the 1998 Draft has a 6.4 handicap, while Brady’s is at 8.1. We’ve also seen what Manning can do in a PGA setting far more recently than we’ve witnessed with Brady, as Manning finished in a tie for ninth this February at the Pebble Beach Pro-Am. Heck, even Brady admits that Manning might have in beat in this particular arena of sport.


As for the real golfers, it hasn’t exactly been a 2020 to remember. Obviously, neither has had much of an opportunity to showcase their skills with several tournaments having been postponed in recent months; yet both Woods and Mickelson had faced some hardship prior to the Tour’s standstill. For Tiger, a nagging back injury had restricted him to playing in just two events this year. For Phil, the issue was more about on-course results. Though the lefty did manage to finish third at that aforementioned Pro-Am – at a course he’s always dominated – Mickelson has actually missed the cut at four of the last five tournaments he’s played in. A list that includes The American Express, The Farmers Open, The Genesis Invitational and The Arnold Palmer. Considering that Woods has had some time to recover, that he’s a member at Medalist Golf Club, and that he might be playing with the better partner; it’s easy to understand why he and Manning are seemingly the consensus pick to win.

Free To Play: Tiger Vs. Phil $50K Guaranteed Pool Analysis

DK Live’s Geoff Ulrich provided his analysis on the DraftKings Sportsbook Free To Play: The Match – Tiger vs. Phil 5/24 $50K Guaranteedwhich you can enter until it locks on Sunday, May 24th at 2:00 p.m. ET. Below, we include two excerpts from his article with analysis.


Let’s first address the elephant in the room. Phil Mickelson won the first version of The Match in a playoff over Woods last year. Right off the bat that has me wary of betting against Tiger, as I have serious reservations that an Alpha competitor like Woods won’t be taking this event seriously to avoid Phil having a 2-0 record against him. Secondly, the current DK Sportsbook odds do list Woods and Manning as -225 favorites, and while I recognize the +180 on Phil and Brady don’t make them huge underdogs, it’s worth noting that Manning’s had a lot more time than Brady to work on his golf game the past couple of years and has a better handicap than Tom. From a Pool and strategy standpoint, Tiger and Manning will likely be the more popular choice, but I’m not confident enough in Phil and Brady to go against them and would look for other props to differentiate yourself.


Obviously, we have to think about how the Match may progress when answering questions pertaining to who will be in the lead after a certain number of holes. As mentioned above, I like Tiger and Manning to eventually prevail, but that doesn’t mean they will be holding a lead the entire match, especially with a change in format after nine holes. For the best ball portion, I think Mickelson and Brady will have a much better shot at winning some holes and keeping things close and with an easy opening hole and a Par 5 on No. 3, so I like taking Phil/Brady here to jump out to a lead. Phil’s been a great Par 5 scorer for most of his career and should be looking to be aggressive from the get-go given his team’s underdog status.


As for who the leaders will be after holes six and nine, I like taking a tie after six holes and to side with Tiger and Manning after nine. The longer the match goes, the more I like Tiger and Manning to separate themselves and that’s how I think this will play out. These three props will be some of the hardest to nail as we’re essentially being asked to predict the results of each hole on the front nine, so my only parting advice would be, develop a plan of how you think the front nine and entire match will play out and then apply it to your answers. I see a quick start by Phil and Brady, with Tiger and Manning eventually taking control by the start of the back nine.

To read the rest of Geoff’s analysis, go to The Match: Champions for Charity DraftKings Sportsbook Pool Picks and Predictions.

Notable Match Bets

See a full list of all The Match 2020 Prop Bets provided by the DraftKings Sportsbook.

Leader after X Holes

Leader after 12 holes

Woods/Manning: -120 | Mickelson/Brady: +175 | Tie: +450

Leader after 3 holes

Woods/Manning: +125 | Mickelson/Brady: +138 | Tie: +225

Leader after 9 holes

Woods/Manning: -110 | Mickelson/Brady: +175 | Tie: +400

First to go up X

First to go 1 Up

Woods/Manning: -150 | Mickelson/Brady: +120

First to go 2 Up

Woods/Manning: -175 | Mickelson/Brady: +138

See a full list of all The Match 2020 Prop Bets provided by the DraftKings Sportsbook.

Hole in One in the tournament

Yes: +5000

Hole on which the Match will be won

Holes 15-17: +110 | 18th Hole or Extra Holes: +175 | 14th Hole or earlier: +300