Gary, who plays at Penrith Golf Club in Cumbria was a member of the Great Britain and Ireland Walker Cup team in 2005. Gary led the English Order of Merit as a result of outstanding performances in the major amateur stroke-play tournaments in 2005. He won the Lytham Trophy, finished in a share of third place in the St Andrews Links Trophy and partnered professional Paul Jenkinson to win the Sunningdale Foursomes. Gary also won the English Amateur in 2003.