After winning first prize in the Gutshot Poker Festival, Roland went on to make a money finish in the $1,000 No Limit event of the 2005 World Series of Poker. In July 2005, he won first place in the Grand Prix de Paris event of the World Poker Tour (WPT)'s fourth season, defeating former champion Juha Helppi in the final heads-up battle. In April 2006, he finished 3rd out of 605 runners in the WPT $25,000 Championship event at the Bellagio, winning over $1,000,000. In October 2006, De Wolfe won the European Poker Tour (EPT) Dublin event, and the €554,300 first prize. In the process, he became the first person to win an event in the WPT and the EPT. As of 2007, his total live tournament winnings exceed $ 3,359,745.