Good news for anyone who likes golf, random stats, and proving they know more ball than their friends.

We’re happy to announce that we have built four free Golf Trivia games on Caddyshanks. They are live now, they are free to play, and we want you to try them out.

Eventually, we think it would be pretty cool to have a monthly leaderboard with golf prizes. Maybe a winner every month. Maybe some gear. Maybe eternal bragging rights. We’ll see where it goes.

For now, we just want you all to test them, play around, and give us feedback.

For example, if today’s games are way too easy, you can tell us. If they are broken, definitely tell us. If you get hooked and waste 20 minutes trying to remember who gained more strokes putting in 2023, that is technically the point.

Here Are The Four Games

Big Board

Rank ten golfers by a specific stat.

Sounds simple. Then you realize you have to decide whether Brian Harman or Tommy Fleetwood had the better number in a category you only pretend to understand.

Scouting Report

Guess the golfer based on the clues.

You get three tries. Use them wisely.

Going Streaking

Pick who had more and keep the streak going.

It is very easy to feel smart after two correct answers. It is even easier to get humbled on the third.

Mileage Marker

Guess the distance between two golf courses.

This is for anyone who has ever looked at a map and said, “Yeah, that’s probably only like two hours away,” before ruining an entire golf trip itinerary.

Go Play

The games are free, they are live, and we’d love your feedback as we keep building them out.

Play Games Here

You’ve probably never heard of Marcus Plunkett, but his journey to The Open is worth noting. Plunkett graduated from West Point in 2016 where he played golf. After Graduating he would go on to serve his country stationed in far away lands and ultimately doing a six month tour of Afghanistan.

As his military career started to wind down in 2021, he did what all men with more time on their hands do, become an alcoholic. Just Kidding. He got back into golf and decided he wanted to make a go of it and become a pro.

After excelling on the Dakotas Tour, he gained status on the Korn Ferry Tour. However he failed to make 12 of 20 cuts and all of his 7 world ranked starts have come in Asia where he has tied for 6th twice.

At the 36 hole final Qualifier at Dundonald Links course in Scotland, Plunkett put a 69, and a 72 on the score card putting him at 3 under par and tied for fourth. It also got him a spot in his first major. We’ll be rooting for him to qualify and stamp his name firmly in the history of Golf.

Every golf trip eventually has the same moment.

Someone is standing next to the cart after 18 holes, trying to figure out who won what match, how many points that means, who still has a chance tomorrow, and whether Dave was actually getting a stroke on 13 or just made that up somewhere around the turn.

That person is usually the same guy every year.

He brings the spreadsheet. He makes the teams. He tracks the matches. He answers 14 different versions of “wait, what do we need here?” He becomes the unpaid commissioner of a golf trip that was supposed to be relaxing.

That’s where CupTracker comes in.

CupTracker does one thing, and it does it very well: it runs your Ryder Cup-style golf trip from start to finish.

Not your swing. Not your stats. Not your tee time booking. Not your range session. Just the actual team competition that turns a regular buddy trip into something everyone talks about for the next 11 months.

If your group does teams, foursomes, fourballs, singles, handicaps, side matches, and a live leaderboard, CupTracker is built for you.

Built For The Buddy Trip Commissioner

Most golf apps try to do everything. CupTracker is different. It is built for one specific type of golf event: the annual buddy trip where the boys pretend they’re at Bethpage, Whistling Straits, or Marco Simone, except the opening tee shots include breakfast beers and at least one guy wearing joggers he absolutely cannot pull off.

The best part is that it removes the worst part.

No more scoring math on the back of a scorecard. No more group texts trying to figure out the standings. No more one guy disappearing into a spreadsheet for an hour after dinner while everyone else is asking if singles pairings are out yet.

CupTracker handles the live scoring, automatic handicapping, custom formats, and live leaderboard. Everyone can follow the event from their phone, which means the trip immediately feels more official.

And let’s be honest, that’s half the fun.

Make The Trip Feel Like A Real Event

A Ryder Cup-style buddy trip is not just about playing golf. It’s about the scoreboard. It’s about knowing your match matters. It’s about standing on the 17th tee with your team watching and realizing you have to hit the fairway even though you have not done that once all day.

It’s about turning a normal round into something with a little juice.

CupTracker makes that easier to run.

The app was originally built three years ago for the founder’s own annual trip. Since then, it has scored more than 1.6 million holes across real tournaments.

That’s a lot of conceded three-footers. And probably a few that should not have been conceded.

What used to take an hour of spreadsheet work now updates in real time. Matches move. Points change. The leaderboard shifts. The group can see exactly where things stand without waiting for someone to do math while holding a half-eaten sandwich.

The Upgrade Your Annual Trip Needs

For trip organizers, that’s the real win.

Because running one of these events is fun in theory, but it can become a full-time job pretty quickly. You have to build the teams, apply handicaps, set the formats, track the matches, keep score, update standings, and explain to the same four guys every year what fourball means.

CupTracker takes a lot of that off your plate.

So if your group runs the same trip every year, or you’ve been talking about finally doing a Ryder Cup-style event, this is the upgrade that makes it feel like a real tournament.

Not “Jim made a spreadsheet and we think Team Red won.”

A real tournament.

Live scoring. Real-time standings. Custom formats. Automatic handicapping. All in one place.

Basically, it lets your group enjoy the fun part of a Ryder Cup-style competition without turning one guy into an unpaid assistant captain, rules official, accountant, and IT department.

Use code CADDYSHANKS for 10% off, good through the end of September.

Download CupTracker here.

Earlier today Scottie Scheffler and Viktor Hovland squared off in a sudden death playoff to see who is the Travelers Champion. With Hovland and Scheffler both looking at makable birdie putts there was air that this could go some distance. Unfortunately, Hovland drained his and Scottie two putted, how dare he? I love a playoff and was hoping it would go on forever. It didn’t so I decided to search the greatest playoffs in the history of golf. Here they are:

1. 1913 U.S. Open (The Country Club, Brookline) Francis Ouimet def. Harry Vardon and Ted Ray

If you love golf movies or golf history you know this story. Widely considered the greatest match ever played. The 20 year old amateur Francis Ouimet took down Two British legends who had both won the U.S. Open in the past. After 72 holes the three were even ,and at the time the Playoff was a full 18 the next day. Through rainy conditions, the heavy underdog and his 10 year-old caddy finished one under with a firm 5 stroke lead. The match was an amazing story that catapulted golfs popularity in America. Amateurs everywhere owe Ouimet a debt of Gratitude.

2. 2000 PGA Championship (Valhalla) Tiger Woods def. Bob May

3. 2008 U.S. Open (Torrey Pines)  Tiger Woods def. Rocco Mediate

Woods played on a torn ACL and stress fractures, forcing an 18-hole playoff with a dramatic birdie on the 72nd hole, then winning on the first sudden-death hole. It epitomizes resilience and is often called one of the most compelling major finishes ever, blending physical drama with elite competition.

4. 1987 Masters  Larry Mize def. Greg Norman (and Seve Ballesteros)

Final Thoughts:

Now there’s a lot we missed that maybe could of made it. But we chose these five based on the history, who was involved and what the event was. Obviously majors take precedent. We would love to hear what your favorite playoffs are, sound off in the insta comments

Tiger Woods made his first public appearance Tuesday since his March car crash and arrest. He introduced Brian Rolapp ahead of the TOUR’s big announcement today.

And the PGA TOUR is finally doing the thing it has been hinting at for months: blowing up the schedule and starting over.

Beginning in 2028, the TOUR will move to a two-series model. At the top will be the PGA TOUR Championship Series, where the best players will play the biggest events. Under that will be the PGA TOUR Challenger Series, which will basically become the path for players trying to earn their way back into the big boy room.

The Championship Series will run roughly February through August and include 23-24 events, with the majors, The Players, team events, and a reworked postseason all folded in. These events will have 120-player fields, 36-hole cuts, and minimum $20 million purses.

So yes, cuts are back. Praise be.

The Challenger Series will have at least 20 events, 144-player fields, 36-hole cuts, and minimum $4 million purses. The top 20 players from that series will earn promotion each season, while the top 90 in the Championship Series will keep their spots. Win twice on the Challenger Series, and you can earn your way up immediately.

There will also be a “last chance” fall series for players trying to hang onto, or regain, Championship Series status. Think of it as golf’s version of a playoff for your job.

The TOUR Championship is changing too. East Lake will still host this year and again in 2027, but after that, the event is expected to rotate to “prestigious courses.”

And not just regular prestigious. We’re talking Pine Valley, Cypress Point, and Seminole.

For decades, golf fans have heard about these mythical places, but unless you knew a guy who knew a guy whose grandfather invented municipal bonds, you probably weren’t getting anywhere near them. Now, we may actually get to watch the best players in the world compete there with a trophy on the line.

Also, Match Play is expected to become part of the TOUR Championship picture, which is another welcome change. It will add some drama to what has become a lifeless end of season experience for fans.

Sign us all the way up. These changes are overall pretty small, and all of them are pretty fan forward, at least on the surface.

Rory McIlroy also released a statement supporting the new structure, saying:

“Today’s announcement is a positive step for professional golf. As more details emerge, it is encouraging to see the PGA Tour reaffirming the importance of meritocracy and creating a structure that will serve both players and fans well into the future

“I’ve always been proud to compete around the world, and the collaboration between the PGA Tour and DP World Tour is one founded in the betterment of the game globally. The commitment to elevate some of these historic international tournaments and national opens is incredibly important for the game and something I’m very supportive of.

“Over the last few years, golf has faced a period of uncertainty and division, which has not been in the best interests of the players, or the fans of the game. Today, we are putting the fans first, and I am excited about the future of our sport.”

Now, this is the same Rory who made headlines at the U.S. Open for calling the new Track 2 system “glorified Korn Ferry events,” so there is at least a little bit of message-board whiplash here.

But his larger point is probably the right one. Golf has been stuck in a weird, exhausting, political mud fight for the last few years, and fans have been the ones left trying to make sense of it.

In plain English: the PGA TOUR wants fewer meaningless weeks, more best-on-best golf, clearer stakes, and a real promotion/relegation system.

In even plainer English: the rich get richer, the middle class gets nervous, and golf fans may finally get a schedule that is easier to follow.

There are still plenty of details to figure out, but the direction is clear. The PGA TOUR is trying to become more like a real sports league.

Whether that fixes everything?

We’ll see.

But at least “Signature Event with no cut and half the field missing” appears to be headed for the big leaderboard in the sky.

Keith Mitchell finds himself at even par after the first 18 on Thursday. Not crazy, unless you watched how he got there.

Holes 10-18

Starting on the 10th hole at Shinnecock, he proceeded to double bogey (we accept you, one of us).  Unfortunately for him, the next 8 holes would include 4 more bogeys & zero birdies. He even bogey’d the par 5 on hole 16. Which if you’ve never heard Tigers tips for lowering your score he is vehemently against bogeys on par 5s.

Mitchell would end up shooting a 41 (dream 9 for me) on his first 9. Not gonna lie they had him in the first half.

Holes 1-9

Then somehow the sun shined through the dark clouds and found Mitchell’s game. Mitchell would go on to shoot a 29 on through his last 9,  Totaling 4 birdies, 1 eagle, & zero bogeys. Absolutely incredible golf by him when he needed it most.

Final Thoughts

I have obviously never played 9 as good as his awful front 9 today. But I have to imagine Mitchell returns tomorrow with the confidence to keep it going. Golf is tricky though and anything can happen. I’m hoping he’s dialed tomorrow for all 18.

Last thing: Guy had a great fit today. Looked like pure class, gotta think that had something to do with his back 9 come up.