Tiger vs. Phil Expert Picks: How to Bet ‘The Match’

Tiger vs. Phil has been hyped as a match made in heaven for bettors, and judging by the six-figure side action already thrown around by the two legends — and the number of different prop bets posted around the betting market — it certainly hasn’t disappointed.

True to form, our golf experts will have plenty of action on “The Match.” Here are their favorite wagers of the bunch.

All odds as of 10:30 a.m. ET on Wednesday morning.

Drew “Sleeze” Stoltz: Under 21.5 cuss words (-115)

Let’s be honest: Tiger and Phil are doing their best to stir the pot with some competitive banter leading up to this match, but their “24/7” episode on HBO was about as far from “Mayweather/McGregor” as they normally are from the fairway.

While we all know Tiger isn’t afraid to let a few “F-bombs” slip when he isn’t mic’d up, he’s not going to be letting them fly when he knows the entire sports world is listening to every word he says. If he didn’t use any profanity in the 24/7 episode, don’t expect much in the match itself.

As far as Phil goes, I can’t ever remember him being caught cussing on camera. I don’t think he’s going to use this event as a coming out party, especially when every prop bet involves a charity of some sort.

Can you imagine him losing a closest to the pin contest and saying, “S—! I don’t want to help save the whales!” Me either, although that would be awesome.

My guess is they both throw a few harmless four letter words out there early on to give it a behind-the-scenes vibe, but the two biggest brands in golf are too smart to go overboard with it.

Hammer the under, God damnit.

Justin Bailey: Phil Mickelson misses the fairway on hole No. 1 (+135)

There isn’t any value on betting Phil to hit the fairway (-165), so throwing out a bet on him missing at +135 sounds like the optimal play. Mickelson isn’t known for his accuracy, hitting just 52.9% of fairways over his past 90 rounds, which ranks 189th of 193 qualifying golfers. Additionally, over his past four rounds, he’s hit just 41.1% of fairways, ranking T-291 of 295 golfers.

Jason Sobel: Tiger will hit hole No. 1 fairway (-195); Phil will hit hole No. 1 fairway (-165)

I’ll take the other side on Justin’s bet, plus sprinkle in some on Tiger to hit the first fairway, too.

Mickelson has already stated that he'll probably just knock a 2-iron down the fairway (and that he'll birdie the hole, an assertion he's backed up already with a $200,000 side bet).

Woods likely won't hit the big stick here, either, which makes this an easy call. Take 'em both to find the fairway — and if you can find a shop that’ll let you parlay these together, go ahead and do it without second guessing.

Joshua Perry: Tiger or Phil will win three straight holes (+600)

With Tiger a clear favorite at -200, there’s a decent chance this match isn’t close. Tiger’s game is just in much better shape than Phil’s at the moment. But instead of backing Tiger to win 5&4 or 4&3 at bigger odds and trying to get lucky with the exact score, I just settled on this spot.

Looking back through match play events this year, four of the 12 Ryder Cup singles matches had streaks of three or more wins. Meanwhile, at the WGC event, five of 16 knockout stage matches featured three straight holes won for a player. The odds of this hitting are probably closer to +200 or +300, so the bet has some value at +600.

Evan Abrams: Match will not go to a playoff (-300)

Laying juice normally isn’t my thing, but in this case, I do think there is value in taking the match not to go to a playoff. There are numerous scenarios under which this could end before the 18th hole.

As the players make the turn, I expect them to take a few more risks. That should create a little volatility in the scores and thus some separation between the two. Plus, let's be honest, the last thing both Tiger and Phil want is to play more than 18 on a Friday night in Las Vegas.

Bryan Mears: Tiger Woods to have longest tee shot on hole No. 7 (-135)

Shadow Creek has a bunch of holes on which these guys might not push it with their drivers. Hole No. 1, for example, has a creek on the left side for the entirety of the hole, which means they’ll likely play it safe with a wood or iron.

The one hole they’ll definitely let it fly is No. 7, which is a steep 570 yards but it should be reachable in two if they’re aggressive. Tiger is definitely longer than Phil, who has lost distance over the years, and I think this is the hole Tiger really puts some muscle into it.

Peter Jennings: Donald Trump will not be in attendance (-1000)

I brought this prop up on our props podcast, jokingly saying I would bet half my net worth on Donald Trump not showing up to the match.

After hearing Sobel and Sleeze raise additional points, I seriously would go all-in on this prop if I could (I’d imagine it carries small limits at BetDSI).

Jason pointed out that there was nothing unusual about applying/receiving his press pass for this match, which hasn’t been the case in the past when he’s attended tournaments with the president in attendance.

Sleeze also brought up the danger of Trump getting hit by a wayward drive which we know Tiger and Phil are capable of.

This is bet is a LOCK. I hope I can invest more than $100 on this prop.

Scott Miller: Tiger Woods will win the match (-190)

I’ve heard all the cases for Phil — and I buy some of them — but I don’t agree that he’ll be more motivated for "The Match." Does his gambling mentality give him a leg-up in the side action bets the two will be making? Absolutely.

But that stuff is the side dish in this shmorgishborg of gambling goodness. The real prize is that $9 million check that will go to the winner.

And if there’s one thing we know about Tiger Woods, it’s that he loves money. Remember, this is the same guy who decided to fly 17 hours to Dubai when he was struggling with back issues simply to cash a seven-figure appearance fee. To the surprise of no one, that trip ended up causing another setback before his eventual return to form.

If he's that motivated for $1 million, imagine how revved up he'll be for $9 million.

Tiger might not have prepped as hard for this event as Phil, but he has been playing MUCH better golf coming into it and knows the course well from hosting his Tiger Jam charity event there over the years.

My parting advise is to wait and see if this number comes down a tad. I like it up to -200, but think we'll see some square money flood the underdog lefty on Friday, giving Tiger an even more desirable price.