Match3

DraftKings is offering up another Free to Play Pool on the DraftKings Sportsbook and this time it’s based around the upcoming “Match” between Tiger Woods and Phil Mickelson. The Match II will feature Woods and partner Peyton Manning squaring off against Mickelson and partner Tom Brady. The event takes place at Medalist Golf Club in Hobe Sound Florida on May 24.

To celebrate, DraftKings is offering a free-to-play pool on DraftKings Sportsbook that enables its users to get in on the action. To participate in the free pool, choose winners on each of 12 unique props offered up by the contest and compete for $50,000 in prizes.

I’ve compiled a list of answers to all the props and questions you’ll be asked to answer in the Free to Play pool. The four men will be playing in partners in a match-play format with the front nine consisting of a “best-ball” format, while the back nine will be played as an “alternate shot,” where each team will play just one ball between them. With two amateurs playing that should create a lot of interesting dynamics.

Head here to participate: FREE TO PLAY: THE MATCH 5/24 – $50K GUARANTEED

Here are my thoughts on each of the props in the pool.


Who will win the match?

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.


What will the outcome of the first hole be?

As mentioned above, there will be other places to go against Tiger and Peyton, who are likely going to be the popular pick in this pool on many props. This one might be a good spot to go against them though. The first hole on Medalist is a 397-yard Par 4 and is listed as the fourth easiest hole on the scorecard in terms of overall handicap. Seeing a quick birdie out of the gates by Phil here wouldn’t shock me as the short Par 4 should give him a chance to be aggressive and take a quick one-up lead. While a halve is the most likely scenario, going with what is likely to be the least picked option here, in a Phil/Brady win on the first hole, has some appeal to me even though I like the team of Tiger and Manning to prevail in the long run.


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Which team will go 2 up first?

The course will get significantly hard after the easy first as holes 2-6 are four of the nine toughest on the course. I think these tough holes are where Manning and Tiger will start to differentiate themselves as they do have a bit of a skill edge, especially with Phil coming into this match having missed four of his past five cuts on the PGA. Additionally, Tiger is now 55 spots ahead of Phil in the OWGR, which just goes to show the difference in the level of play between these two the past couple of years. While both men may have a little rust to knock off given the hiatus, they’ve both been on from playing competitively, I’ll still take the Woods/Manning team to prevail here as they seem far more likely to get out to a significant lead at some point than Phil/Brady.


Hole 3: Who will hit the longer tee shot?

Hole 13: Who will hit the longer tee shot?

The third hole is listed as a 553-yard par 5, so both of the pros here — we’re just picking between Tiger and Phil on this one — should be able to grip and rip a driver off the tee. Phil has been well documented for his penchant for hitting “bombs” on the course, even as he advances near the age-50 mark. Despite Tiger winning the Masters last year, Phil did average 10 yards more off the tee in 2019. Even though we’ll have to avoid a patented Lefty “tree-ball,” going with the stats here and the aggressive Phil does seem to make the best sense on this one.

As for Hole 13 where we’re being asked to pick between Brady and Manning, this one seems a bit trickier because we’re dealing with two amateurs who will be highly inconsistent in their ball-striking compared to their partners. That being said, Manning’s handicap has been reported to be anywhere from two-four points better than Tom’s and with that big a gap I’d have to side with Manning on this one.


Hole 4: Nearest to the hole after tee shot?

Will any golfer hit a hole in one?

We get to choose between all four golfers on this one and even have an option to choose “no player hits the green.” Right off the bat, I’d be fine crossing that last one off my list. The fourth hole is listed as a 190-yard Par 3, but also is the second easiest hole on the course, handicap-wise, so seeing all four players miss the green here seems highly unlikely. One thing that has really stood out in Tiger’s return has been his iron play. He’s consistently been ranked inside the top 10 on Tour in SG: Approach stats while Phil was ranked a disappointing 122nd on Tour in this stat last year. Woods also dominates Phil in Par 3 scoring stats overall the past couple of years, so Tiger would be my choice here between the pros. If you want to get wild though and try to differentiate yourself a bit in the pool (remember there will be a lot of entrants), going with Peyton Manning doesn’t seem like the worst idea. He’s the third-best golfer of the group and is certainly capable of upstaging the pros on one shot.

As for the hole in one question, pro golfers’ odds of hitting a hole-in-one have been calculated to be anywhere from 1,000-3,000 to 1, while amateurs’ odds are much higher. I’m OK fading that big a long shot and it should be mentioned that only one of Medalist’s Par 3s measures in at under 200 yards. Take the no and move on.


Leader after 3 holes?

Leader after 6 holes?

Leader after 9 holes?

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.


Will either team make an eagle in the match?

First golfer to hit a ball in the water?

Medalist does have four Par 5s on its scorecard, but I’d still take the no on this one. The catch here is that the entire back nine will be played as an “alternate shot” and while one of Brady or Manning could come up with a miraculous shot or putt to sink an eagle, I’d rather not rely on the amateurs. The second factor is the course. Medalist’s Par 5s don’t appear to be easy with the Par 5 seventh hole listed as the easiest of the three-shotters, but as just the eighth easiest in handicap on the course. The Par 5, 13th is listed at 610 yards in length and from a handicap perspective, the second hardest on the course. I’ll take the no here.

As for who will hit the water first, I think Phil makes for an easy target. Many competitors will be going after the amateurs here but with this event being live on TV Peyton and Tom may tone down the aggressiveness in spots to avoid getting wet. Phil won’t be toning down anything though and, as mentioned above, he only ranked 122nd in SG: Approach on Tour last year. Give me Phil to give us the first water-ball of the competition.


I am a promoter at DraftKings and am also an avid fan and user (my username is wavegoodbye) and may sometimes play on my personal account in the games that I offer advice on. Although I have expressed my personal view on the games and strategies above, they do not necessarily reflect the view(s) of DraftKings and I may also deploy different players and strategies than what I recommend above.


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