Best Golf Gambling Stories

Let’s share some good breaks and bad beats. It can be your story or someone you know, or just somebody you heard about!

Here’s my biggest loss:

$10 dollar base wolf game with hammers playing a tight par 4 that doglegs right. I tee off first and crush a drive over the corner to about 100 yds out staring down the pin.

The next three guys proceed to tug their drives left, and I assume they are blocked out and will all need to take medicine. LONE WOLF HOWL ENSUES.

The bet is now $20 per man and as its 1 vs 3, I am on the hook for $60 dollars.

While I am standing in there fairway thinking about making birdie to double these knuckleheads up and make a lot of dough, the first two guys punch out and take their medicine. The third guy says he has a window. Now the third guy is a 14 handicapper at best, has 130-140 yards, tree trouble and has to carry a bunker on the front of a 15’ elevated green. The guy hits a punch shot, two hops in front of the bunker, dives perfectly in, rolls up the lip and pops out onto the green. Truly a MIRACLE shot.

At this point I get hammered. OH SH*T. While he hit a good shot, I am pretty sure that he is not stiff and is probably at least 10ft out. I accept. I act like I was this logical at the time, but there was no way I wasn’t accepting. Pull out the gap wedge and hit it decent. Elevated green so I am thinking I am likely in the 10ft to 20ft range

We get up there. I am about 20ft, he has about 15 ft. Both hitting slightly down hill left to righters. Odds are that we push the majority of the time. I do have the hammer, which could be quite the advantage if I drain it. As I mentioned, I am putting up $120 at this point.

I hit a solid putt, looked like it may have a chance, but in the last 10 ft the read was off by 3 or 4 inches and my ball rolls a ft by harmlessly. This guy steps up and trickles a putt down the hill that stops on the edge of the cup for a heartbeat and then drops in.

DAGGER

This jabroni made birdie from the trees rolling a ball through a sand trap and burned me for $240 on a single hole.

Far and away the largest wager I’ve had on a hole. This was not my typical group and these guys usually play for about 2x the stakes we played today ($20 and $50 base wolf). It’s very rare for me to win/lose more than $50 with our typical group. I scrapped back that day and ended up down maybe $100

Live and learn. Lone wolf is dangerous.

“Good judgement comes from experience. Experience comes from bad judgement”

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I don’t have any great stories but if you haven’t read the novel, The Green, by Troon McAllister, you are really missing a good one.

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Probably going to butcher this story since my memory of it is a little fuzzy and can’t figure out the exact math, but I’ll try (you’ll get the gist).

Mentioned on another topic I like to play Scotch w/ 4 bets a hole (can explain if needed). Well one day we’re playing with 5 people and decide to make up a game - Wolf Scotch. I forget how we did the specifics, think you couldn’t go solo (since there wouldn’t be a team score). Difficulty in this is that inherently the Wolf is at a disadvantage since you’re going 2 on 3 every hole so the 3 man team can kick out a bad score and has 3 chances at birdie/closest to pin/low man.

Since there were 5 of us we said we’d play through 15 and then reset where last place gets to be wolf on 16-18 (resetting each hole) and they could reset the amount of the bet. I think 1-15 it was $.50 a dot.

Anyway, through 15 I’m down probably $40 since kept getting picked by the wolf on holes that the other team swept and picked up big $. Wasn’t playing great, wasn’t playing bad - it was just that we made this game up and it was not working out for me.

Anyway, on 16 I’m up first and I kept the bet as is - just trying to cut my losses at this point. I’m still in last going to 17 and do the same thing, no change to bet.

On 17 I won a little so was 2nd to last and another guy got to go first. We’re both down around $40 at this point.

On 18 tee (short par 4) he ups the bet to maybe $8/point and hits his drive in the middle. I hit next into right rough but he picks me since we need to gang up on the other guys. Don’t remember exactly how we set up the rules for this 5 man wolf scotch, but however we did it, we were allowed to press - so he did. Now each point is $16. Two of the other 3 are in good shape and one is in the trees (out of the hole).

Both guys on other team hit green but not very close. I flub my 60 yard shot into the green (ugh). Partner then hits his shot to 5 feet (winner for closest to pin!). My 3rd gets on green but probably 40 feet away (front pin, had to go long).

I drain my 40 footer for par!

Other team 2 putts for pars.

Partner makes 5 footer (birdie winner, individual winner, team winner). We swept all bets so it doubled the bet again! We ended up both walking away with around $80.

Never will play wolf scotch again.

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I’m a big Mickelson fan already, but that story was great! :grinning:

That’s great. I love a good “cry baby” presses on the final few holes.

What’s yall’s setup for scotch four ways? Presses typically allowed? We usually stick to wolf, no hammer, no carries, gross birdies double or simple 6-6-6 match play (birdies double).

Leading team tees off first every hold. Trailing team can press after seeing the leaders tee shots. Leading team can press back after trailing team hits.

Can get very fun.

ALWAYS press on a par 3 if the leaders both miss the green - easy 2 dots if one of you hits the green.

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Biggest win for me was 2 years ago in the Fall Shootout at my club. The top 10 2-man teams after an 18 hole quota format go to the Shootout which is true alternate shot for 9 holes. The high score team on each hole is cut or their is a chip off for ties. The Shootouts have a lot of gambling with teams going for $100 to $1500 each. We were new members and hardly anyone bid on us so we bought ourselves for $300 I think. We ended up winning the whole thing which was a big payout. I didn’t even want to put $50 on us lol.

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Calcutta always has the best payouts!!!

I’m sure y’all caught some flak for having bought yourselves!!!

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No honestly we give people all due credit that buy themselves as that takes guts. My 2 buddies bought themselves in a shootout earlier this year and won. I helped them buy themselves again in the last shootout (they got bid up as past champs do) and they won again. That was a good day for me even though my team didn’t win!

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Sounds like we need to go to the horse track together. You got a knack for picking winners.

I’m usually pretty bad, but I have won more money gambling at the course than playing these last 2 years…of course I’m probably even at best despite some big wins lol.