The 2006 World Championship saw Hamilton gain revenge for his defeat to Anderson last year with a 3–2 first round win. He also knocked out Terry Jenkins 4–1 in the subsequent round. However, Hamilton fell to eventual winner Phil Taylor in the third round losing 4–0. Hamilton did manage to gain a share of the prize for highest three-dart checkout by hitting a 170 finish, a feat matched by Taylor. Hamilton reached the quarter-finals of the Las Vegas Desert Classic before being eliminated by eventual runner-up Raymond van Barneveld 3–1. He had defeated Kevin Painter 6–4 and enjoyed a comprehensive 3–0 victory over Matt Clark in the prior rounds. Hamilton made his Winter Gardens debut at the World Matchplay tournament. He sprang something of a surprise in round one by thrashing number four seed Peter Manley 10–2 and then overcame Adrian Lewis in the second round, the duo produced a thrilling match that eventually saw Hamilton triumph 15–13. Hamilton's fine run continued as he defeated crowd favourite Wayne Mardle 16–9 to reach his first major semi-final. However Taylor, a seven time World Matchplay champion, eliminated Hamilton 17–11 in the semi-finals.