The Most Important Things to Know About Playing Golf for Money

The following is a chapter from my short e-book The Ultimate Guide to Playing “Money” Golf. If you love the content in this section, I truly hope you consider buying the book.

Playing Golf for Money: An Overview

In order to maximize your earning potential playing golf, it helps to understand that many of the decisions necessary to succeed occur outside the course of play.

The first most important decision any golfer can make is the proper selection of games, as well as whom she chooses to play with/against. Not only does this affect your ability to be a winning player, it also determines how much you’ll enjoy playing for money, which is key.

The vast majority of golf leagues and money games utilize handicaps, which can carry a great deal of controversy and headache, depending on the ethical makeup of the group you play with. Having any type of fair game requires honesty from each of its players, ensuring that no one has bloated their handicap beyond their true capabilities, commonly known as sandbagging.

Sandbagging can be easy to spot, but also difficult to avoid. See someone with a pure swing on the course that consistently wins the net score division in your league? Chances are, they have spotted themselves a few extra shots above their true capabilities. Yet, based on how handicaps are weighed, it may not necessarily be cheating in the classic sense. For example, if you played ten rounds with someone, kept their score, and noticed when you looked up their handicap index on the computer that the scores they posted were a few strokes higher, that would be blatant cheating. However, if a player posted honest scores, but only those what reflected when they played bad instead of when they play well, then it’s more difficult to spot.

If you choose to participate in games that favor net scores, the most important question any player should ask themselves is how honest should one be about one’s own capabilities?

The easiest way to pick the right type of game for you is to play in a game that you hear is popular, make a few small wagers, and test the waters. Do the player’s swings seem to match what their handicap claims to be? Are people ruthless when it comes to bargaining strokes for their personal games, not willing to budge when it comes to taking or offering strokes? Your best bet is to find another men’s club or group of guys to play with.

Aside from selecting the right games, there are plenty of other factors to look into.

You want to be someone who people want to play with.

This may be obvious, but the only way you can win money playing golf is to play with people who won’t mind losing to you. Conversely, the worst-case scenario is being someone who only gets action from players who out-match him.

Someone who is rude, egoistical, complains all the time, and pays out like a rigged slot machine is going to be an easy target for those who are better players and can stomach being around him long enough to take his money. Which side of the coin do you want to be on?

Don’t be afraid to give up an edge sometimes.

If you lost every single time you played golf against someone, and they were unwilling to adjust the strokes, would you want to play with them for much longer? I can’t imagine many people would.

Remember the even-money prop I said you should take in the Expected Value section? This is the precise instant where even taking a slight disadvantage will earn you higher EV down the road.

If you have had success against a player or even several players and they propose a different wager, even if it seems to favor them, let it be. If you lose one, it’s not the end of the world, and you avoid making someone feel less like a target and more like a friend.

ALWAYS pay what you owe at the end of a round, and ONLY play in games where everyone shares this “gentleman’s agreement.”

One of the worst things that can happen to any golfer or gambler is being honorable about paying when they owe, but not receiving the same courtesy. This is another instance where keeping your eyes and ears peeled for information about other players can help you avoid being on the bad end of an IOU.


Play in situations where people think you’re worse than you actually are.

If you do find yourself in scenarios where you have to play against unpleasant company, it’s important to let them be themselves and, no matter how much they talk about how bad or lucky you are, to let them keep thinking the same thing.

To be clear, this is not the same as sandbagging. One thing to understand about human beings is there are biases that can skew a person’s analysis of another player.

Here’s an example: Say you have an unconventional golf swing, you’re not the best ball striker, but you make more than your fair share of putts. Even if you are completely honest about your score posting, it’s easy for one to assume that if someone’s golf swing is more conventional or better looking than yours, or hit more greens in regulation than you do, they should be able to beat you.

Ego is the death knell of any serious golfer. Keep yours in check, and allow your opponents to fall into its trap.