Backgammon Plays - Overview
There are three main ways that backgammon can be played, Money Play (i.e., “Backgammon for Money”), Match Play and Chouettes (i.e., “social form of backgammon”). Each of these can be played for money or for “fancies.” As far as playing live or online, that’s discussed below. Money play can also refer to any form where each game is scored separately, even if you're just playing for "points" but there's no money on the line
Naturally, whether playing on real backgammon sets or on virtual ones online, many people choose to play for money.

You can actually watch quite interesting ‘backgammon for money’ games by downloading this Backgammon software application, or by going to the GammonEmpire site and checking out their latest platform for playing online.
Be sure, before proceeding, that you understand both the Jacoby Rule and the Crawford Rule. If you would like a good book that provides more information about these rules, it is recommended that you check out Jacoby and Crawford's backgammon book from 1971: “Backgammon for blood!”.
Backgammon Money Play
In money play, each game is scored separately. You play the game until someone wins, or a double is dropped. You can play a fixed number of games, or for a certain period of time, or just until one player gets tired.
Gammons score double, backgammons score triple. The Jacoby Rule is Gammons almost always used, but this should be agreed to in advance. Beavers are usually allowed, and automatic doubles are sometimes, again these should be discussed.
Backgammon Online Money Play
I’ve had different favorites gaming sites over time. The one I think has done the most of the right things is GammonEmpire. I think have the right mix of ingenuity and trying things that were proven to work. I particularly think they have worked hard to reduce hustling to a minimum. A lot of sites have no apparent rating system, or a rating system where it’s easy for amid players to influence ratings downward. Gammon Empire has a system that is weighted by the money stakes (so a player can't lose low-stakes games and manipulate their rating) and also seems to assertively go after backgammon players with a number of accounts.
Settleing a Game in Money Play
In money play, it is not uncommon to settle a game. For example, suppose both sides have broken contact and the side on roll has 120 pips to go and the other side has 116. Since being on roll is worth, on average, half a roll, and the average roll is 8 pips, the game is basically tied. Rather than rolling the rest of the game to see who rolls better, the players may just call the game off. Or, when the cube gets to high levels, sometimes they may settle the game. Suppose you own an 8-cube and you are on roll, trailing in the race by 80 pips to 68. Your winning chances in this game are about 30%.
You might offer to settle the game for 3 points. On average your opponent will win 70% of the time for +5.6 and lose 30% of the time for –2.4, for a gain of 3.2 points, but he might be happy to lock in a 3-point profit on the game.
It is possible to play a “money game” without actually wagering, but it’s rare. Two people can agree to play backgammon and keep score, without actually wagering money. However, if there is no money involved, it is more common that they will play a match to a fixed number of points, or to just play game by game but not keep score.
Best Plays in Backgammon Money Play - Is it any Different?
It is important to understand what the term “money play” means when discussing a backgammon position. If someone says “For money, the best play with an opening 43 is 24-21 13-9” – it doesn’t mean that they would play one way when money is on the line and another way when it’s not. The best play is the best play! Here’s what it means. In a match, the best play will sometimes depend on the match score. For example, if you are trailing late in a match, you may want to play more aggressively for a gammon, and the best play may be different than if you are leading. The best play “for money” will always be the same, as it doesn’t depend on the match score.
The best play “for money” is usually a good reference point, but again, understand that in discussions of backgammon positions it means a game where all points are equally valuable, not necessarily a game where money is at stake.
Backgammon Match Play (also referred to as Tournament Play)
You play until one player wins a fixed number of points. You can wager on a match – that is, instead of playing for $5 a point, you can play a match to 5 with a $25 wager on the match. But match play rules still apply.
Match play is an agreement to play until one player wins a fixed number of points. Almost all tournament play is based on matches; bakgammon matches in tournaments vary tremendously, from one-point matches to 25-point matches.
You can also wager on a match – that is, agree that the loser pays the winner a certain amount of money. Most live play where money is involved is done in a “money play” format, but some people do play money matches. A lot of online play involving wagering is in a match format though. And a lot of friendly, non-money play is in a match setting.
The only special rule that applies is the Crawford Rule. However, automatic doubles, Jacoby Rule, beavers, and settlements, never apply.
Chouette - The Social Form of Backgammon
A chouette is a social form of backgammon where three or more players play on a single board, with one player playing against all the others. Chouettes generally follow all the rules of Money Play. The Backgammon Chouette Play is explained in detail on my site.
Chouette Live Play
In live play, chouettes are very popular. They are very social. One problem sometimes arises in deciding who can play. Let’s say that 3 players are playing and a very strong player wants to join the game. Some of the existing players might be happy to allow the expert in, some might not want to be involved in a money game (almost all live chouettes involve money – I’ve never heard of one that didn’t) with a player that strong. Sometimes they will allow the expert in but reduce the stakes.
Online chouettes are fun, but they are rare. It requires that everyone in the game be very familiar with chouettes, and that everyone be very focused on the game It also requires a couple of players to take charge of the game and do the recordkeeping. I’m not aware if any sites presently offer software that supports automatic chouettes. Usually it is done by the players chatting at the table.