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In playing a particular hand of poker, a freeroll is a situation that arises (usually when only two players remain) before the last card has been dealt, in which one player is guaranteed to at least split the pot with his opponent no matter what the final cards are, but where there is some chance he can win the whole pot if certain final cards are dealt.
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For the last several years, the largest tournament in the world has been the World Series of Poker Main Event. With the exception of 1992, the US$10,000 buy-in tournament increased in prize pool year-over-year from its start in 1970 until 2007 (the latter a result of the Unlawful Internet Gambling Enforcement Act of 2006, which reduced the number of players winning their seats via online play).