Jackson finished in the money of the World Heads-Up Poker Championship in 2005 (final 16) and 2006 (runner-up.) Along the way he eliminated Juan Carlos Mortensen in the quarter-final and Markus Golser in the semi-final. He also finished in the money of the 2004 World Series of Poker (WSOP) main event and the European Poker Tour (EPT) second season grand final.