6 Board Games That Would Be Fun to Bet On

By Anthony Haage in Entertainment and Novelty
| July 12, 2022 11:11 am PDT
Fun Board Games to Gamble on, Connect $, Dice, and more board game pieces

You might have thought about the possibility of gambling for real money when playing popular board games. Some family members can really get into family game night, already making it high stakes and as though money is on the line.

Gambling on the best board games would kick things up a notch for your friends and family. It would be a great way to add some competitiveness into the mix, but how would it work exactly?

It’s not possible to do this right now, but it could be something that happens in the near future. We’ve seen some exciting things over the history of gambling, so you can’t limit the number of opportunities here.

Let’s look at the famous board games that would be great for gambling.

Top Board Games that Missed the Cut

  • Sorry!
  • Monopoly
  • Uno
  • The Game of Life

Before we get into the top board games for gambling, here are a few that missed the cut for us. These games are all entertaining to play, but the transition into gambling would be tough. The main reason is that most of these games are based on pure luck.

To clarify, you can absolutely attempt to play for real money with these games, but don’t be upset when you’re the one on the unlucky side of things.

If you’ve played Yahtzee before, you would know it’s a game based on your luck rolling dice. Unfortunately, there’s more calculating than strategy, which doesn’t translate well to gambling.

Maybe you can do props like, “First player to get a Yahtzee gets $5,” but there isn’t much else outside of that.

Sorry! is a game where you could reward the first person for getting all their pawns home. There’s the slightest bit of strategy here with the “Sorry!” card, but it’s mainly based on which card you draw.

Monopoly is known for creating hatred between family members, so maybe real money could worsen things. It’s also a game primarily based on rolling dice and card drawing, so most of the game is based on luck.

Uno is a game that has different rules depending on which people you are playing with. There’s also not a lot of skill required to win, but rather just turn-taking. You can give your opponents a +2 or +4 card now and then, but it’s not enough to make it a gambling experience.

Instead of dice rolling, the Game of Life is more focused on spinning the wheel. You spin the wheel to take turns with some card drawing mixed in. The goal is to have the most money at the end of the game, but it’s hard to translate into real money.

It’s not impossible to find a way to gamble on these iconic board games, but luck being the most prominent factor can make things difficult.

Connect 4

The first of our great board games for gambling is going to be Connect 4. Its first copy was sold in 1974 by the American board game manufacturer Milton Bradley. The two-player game’s goal is to be the first to get four chips in a row horizontally, vertically, or diagonally.

Seven columns, six rows, and all the chips make for an astounding 4,531,985,219,092 possible combinations. Certainly, that’s enough to keep you busy for a while, right?

The hardest part of the game is being able to prevent your opponent from filling out their four discs in a row while also setting yourself up for the win.
Connect 4

Sometimes you think all is well and your opponent has nowhere to go, only to see them win the game on a random diagonal chain.

You must simultaneously play offense and defense, with forward-thinking being the key to winning. Setting yourself up for a victory takes multiple tries and likely won’t happen in the first handful of turns.

If you want to turn this into a fun gambling experience, I recommend a buy-in per game.

For example, say you and your friend each put $5 into the pot, and the winner would be rewarded with the accumulated $10. You could also have more people betting on the side of your game, so it’s not limited to two players.

Potential props could be:

  • Who will win the game?
  • Over/Under on how many turns it takes?
  • Will the winner connect more than 4?
  • Will the game end in a draw?

In the end, Connect 4 is one of the most popular board games of all time and translates well into gambling. So, if you have a partner you are evenly matched with, why not add a couple of bucks into the mix?

Betting on Connect 4 isn’t really something people do. However, you’re here due to an interest in gambling. If you can’t wait to get the ball rolling, check out the best real money online casinos to get in on the action.


Another one of the most famous board games is from 1946: Stratego. Strategy is in the name, after all, and a lot is required to win. It’s another two-player game, but it is not as simple as Connect 4.

Each player sits on opposing sides of the 10 by 10 board. Using a divider, you set up your army of 40 pieces facing you so your opponent cannot see them. In the game, your pawns will attack or be attacked, with the higher rank winning the battle. For example, if a 7 attacks a 9, the 9 wins, and the 7 is discarded.

Your pieces will all have a rank on them ranging from 1 to 10. Here’s a breakdown of what your army will look like.

Piece Rank Count
Bomb immovable, only Miner (3) can diffuse 6
Marshal 10 1
General 9 1
Colonel 8 2
Major 7 3
Captain 6 4
Lieutenant 5 4
Sergeant 4 4
Miner 3 5
Scout 2 8
Spy 1 (explained below) 1
Flag (immovable) 1

The goal is to move through your opponent’s army by defeating their pawns. Only the Scout (2) can move an infinite number of spaces, but only in one direction (vertically or horizontally). You cannot move bombs or the flag, while the other pieces can only move one space at a time.

If the Spy attacks any other pawn first (except bombs), the Spy wins. However, if the Spy is attacked first, then the Spy loses. That means you can take down a 10 with your Spy but lose to a 2 if they are in the path.

The goal is to dwindle the opponent’s army to where you can identify their flag. Whoever captures the opposing flag first wins.

To make this a gambling experience, you could use similar strategies to Connect 4, such as a buy-in. You could also have a prop for who’s Spy gets discarded first, will a 8 or higher get discarded by a bomb, and more.

The strategy of Stratego sets it apart from the games that missed the cut, making it one of the best board games for adults.


Catan board game

Although the strategy is the name of the game for Stratego, Catan might have more of it. This game can take anywhere between 1-2 hours to finish, so make sure to be comfortable before it starts.

The game’s object is to be the first to 10 victory points. You earn victory points by building settlements, roads, cities, and armies. There are also bonuses for the longest road or strongest army that could be crucial.

Collecting materials like wool, grain, lumber, brick, and ore will allow you to build those structures. Although dice-rolling is in the game, it’s not a dominant aspect like Yahtzee. Instead, the gameplay is more focused on the moves that are in your control.

For example, you decide where you want to build, resources you could trade, opponents to try and cut off, and more.

Catan takes a lot of patience, but it could be worth your while if there were some money on the line. To make things more interesting, maybe make the pot larger than usual so the winner is left feeling rewarded after their hard work.

You could also bet on who finishes with the most structures, resources, longest road, strongest army, and more.

The game’s first edition was published in 1997, but there have been many variances since then. For example, 3 to 4 players can play in the standard edition, but 5 to 12 can play in the movie edition. This could be perfect for serious players if you’re having a huge game night party.

Top Tip
Since it takes a long time to set up and play, it’s perfect for those nights when the power goes out. It could also just be a way for the family to put their electronic devices down for an extended time.

If you think your family has the brains to be able to play a cohesive game, Catan could be one of the top board games that give a real challenge.


This might surprise some, but Scrabble makes for one of the greatest board games that can be gambled on. It also can hold between 2 to 4 players, so another family member or friend can get in on the action.

There’s an excellent chance you have a Scrabble board or at least heard of the game. It was designed in 1938 by Alfred Mosher Butts, an architect during the Great Depression. It’s one of the most popular board games worldwide, being sold in over 120 countries and 30 languages.

The game is set on a 15 by 15 grid, with each player having seven letters. If you put down a 4-letter word, you grab four replacement pieces from the bag until it runs out. Each letter’s value in the words you play gives you points in addition to the bonus spaces.

You fill the grid with words in an agreed-upon dictionary, and whoever has the most points at the end wins.

Scrabble is a very flexible game, requiring strategy, skill, knowledge, and a dash of luck. For example, you might have an easy word like “the” that you can play, but maybe you have the letters for “thesis” that you can play for more points.

It would help if you also aimed for the bonuses to gain an edge over your opponents.

Thanks to the different aspects of the game, there are a couple of fun betting props you can set up. You can reward the winner, like in all competitions, or use unique props, so everyone has a chance to win.

A bonus for the largest single-word score would be ideal, with “oxyphenbutazone” being the highest scoring word possible.

You could track how many vowels are used and reward whoever uses the fewest. Maybe even reward whoever plays the funniest/most challenging word.

Scrabble’s flexibility makes it one of the most dynamic board games of all time and is great for gambling. However, if you are looking for more challenges, take a look at our guide to gambling on skill games.


Jenga pieces

Scrabble can get tricky due to many combinations and counting factors, so let’s take a step back. Jenga is another one of the great board games that could also be used for gambling.

Although it may seem like a game that could be way older than the others on our best board games list, its publication wasn’t until 1983.

The game consists of 54 wooden blocks stacked on top of each other by 3s. Each player takes turns grabbing one block at a time and moving it to the top. That also makes it more of a survival game than one focused on making it to the finish line.

In addition to surviving, it also takes a lot of hand-eye coordination, agility, calmness, and strategy. The whole thing can come crashing down if you pull out a block too fast.

If you are questioning how sturdy these blocks can be, take a look at the world record of 1,512 blocks being balanced on just one piece.

Jenga is a high-speed and straightforward game to play. If you are looking for more action on your game night, maybe give Jenga a try. You’ll be sure to have your winner within minutes.

With Jenga being one of the best board games to play, there are also a couple of things you can bet on. For example, you can bet on how long the game lasts or who makes the tower fall.

This is a perfect game to play with your children as well. They could learn a valuable lesson of patience and calmness while also having a lot of fun. And for the adults, gambling on the side would also make it entertaining.

Which Board Games Would Be Best for Gambling?

Board games graphic

At the end of the day, these are some of the best board games to gamble on. They may seem simple enough but putting some money on the line can make them very intense. If you want a fast-paced game with quick results, Jenga will be the way to go.

Slower and more strategic games for serious players could be Catan or Stratego. Connect 4 and Scrabble are great games to play; they aren’t too short or long.

Countless other ones could make for great board games to bet on. You can keep it simple by having an entry fee and rewarding the winner with the pot, or you can have unique props for other aspects of the game.

So many different things are available in the gambling world nowadays. For example, the best gambling sites offer bets on Madden simulations, so don’t be surprised to see the top board games there soon.

Until that happens, we can practice at these safe online casinos.



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