By the beginning of November, Blom had recovered his losses; he then challenged Dwan to a heads-up marathon that would take place simultaneously on six tables at a time with over a million dollars in play.

By the end of the first week of play, Blom had gone on ostensibly the largest run in the history of online poker, winning approximately $5 million from Dwan, prompting Dwan to issue a live challenge to Blom at the Full Tilt Poker Durrrr Million Dollar Challenge.

[15] In January 2009, Dwan issued a $1,000,000 challenge to play anyone online, "with the exception of Phil Galfond", heads up for 50,000 hands four-tabling at $200/$400 limits or higher No-Limit hold 'em or Pot-Limit Omaha.

[21] At the age of 19, Dwan cashed in at his first live tournament, finishing 12th in the £3,000 no limit Texas Hold 'em Main Event of the European Poker Tour's second season held in London, earning £7,000 ($12,398).

[22] Dwan finished second to James Michael Sowers at the 2008 WPT Borgata Winter Open in the preliminary $5,000 No Limit Hold 'em event, earning $226,100.

[22][23] Dwan cashed twice in the first year that he could to play in a World Series of Poker (WSOP) event held in the United States.

He nearly made another in a seven-person final table, but finished again in 8th, this time in the $5,000 No Limit 2–7 Draw with Rebuys event, earning $45,110.

[22] Dwan participated in the 2008 NBC National Heads-Up Poker Championship held at Caesars Palace Las Vegas, where in his first match he defeated Phil Hellmuth in the third hand.

[24] At the 2008 Five-Star World Poker Classic (the $25,500 WPT Championship), Dwan finished in ninth place, winning $184,670.

He was, however, present in two events including the Third Edition of the Triton Super High Roller Series in Manila and was seen in company of Daniel Cates.

Running from March 17 to 20, the Super High Roller saw Dwan lose the final against Belarus player Mikita Badziakouski.

[citation needed] The final round pitted Dwan against George in an exclusively Texas hold 'em match.

In November 2009, Dwan became a member of Team Full Tilt and re-signed as a brand ambassador for the site on October 15, 2012.

[43] Tom Dwan challenged the undefeated Phil Hellmuth in round 2 of the High Stakes Duel III by Poker Go.

[44] The pair have agreed to a third round at double the stakes to take place in Las Vegas at some point during the 2021 World Series of Poker.

Galfond mentioning that Dwan is factoring in bits and pieces of information at a speed and depth of thought that is "ridiculous".