Chan won the World Series of Poker (WSOP) in (1987 and 1988). A videotape of the 1988 WSOP final heads up match is featured in the movie Rounders, in which Chan makes a cameo appearance. He almost won a third consecutive title, but finished in 2nd place in 1989 to Phil Hellmuth. He is the last player to win back-to-back WSOP Main Events. Jerry Buss, who was an avid poker player and owner of the Los Angeles Lakers, promised Chan an NBA championship ring if he could win three in a row.
In 2005, Chan became the first player to win ten World Series of Poker bracelets, defeating Phil Laak in a Texas hold ’em event. He is currently tied with Doyle Brunson and Phil Ivey for second place with 10 World Series of Poker bracelets, behind Phil Hellmuth (14). He was inducted into the Poker Hall of Fame in 2002.
In 2008, Chan cashed for the first time in the Main Event since 1992, earning $32,166 for his 329th-place finish.
In 2010, Chan cashed in the Main Event taking 156th place for $57,102.