During a reserve team game for Wimbledon in 2000, Earle sustained a heavy blow to the stomach and became seriously ill with a ruptured pancreas. At the age of 35 he was forced to give up playing in November 2000. His retirement coincided with the end of the 'Crazy Gang'. In nine years as a Wimbledon player, he made 244 league appearances for the South London club, scoring 59 goals. Towards his end of his time at the club he began coaching the reserve team.