[This is from one of my posts on Quora]
There are 3 different places that I would recommend for playing online. All of these support match play, hold tournaments, and all support exporting log files of your matches to a format that can be analyzed by desktop backgammon software, like GNU Backgammon and eXtreme Gammon
The first is GridGammon. GridGammon is where the United States Backgammon Federation (USBGF) holds all of their online tournaments. Consequently, there are many top-level players who play there. As mentioned in other posts, GridGammon was derived from GamesGrid, which used to be one of the most popular places to play backgammon for money until playing for money became illegal in the US and GamesGrid was shut down. GridGammon does not allow playing for money, so all of the USBGF tournaments are free to enter. Registration is by invitation only, but the easy way to get an invitation is to sign up for a USBGF membership. GridGammon requires software that you can download for free, but unfortunately it only runs on Microsoft Windows as of now.
If you don't want to join USBGF and/or can't play on Windows, then my next recommendation would be First Internet Backgammon Server (FIBS). FIBS is free and anyone can join. You just need to download one of many client programs. Different client programs have different features and interfaces, but they all connect to the same server. On Microsoft Windows, I would recommend Fibzilla.
My third choice would be DailyGammon. With DailyGammon, instead of playing one live match all the way through at once, you play just a move at a time in many different matches. You make your move whenever is convenient for you during the day (or week) and your opponent makes their move whenever they get online next. So matches can drag on for weeks, but that's why people play dozens of matches at once. One of the nice things about it is that you don't have to commit to playing a whole match at once, you can just play a few moves in a few minutes if that's all you have time for. Another nice thing is that its all browser-based, so there is no special software to download.
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