A former youth player with Stoke City, Earle broke into the professional game with Port Vale in 1982. He spent nine years at the Burslem based club, helping "The Vale" to promotion out of the Fourth Division in 1982–83 and 1985–86, and out of the Third Division via the play-offs in 1989; he was later voted the club's PFA Fans' Favourites. He moved on to Wimbledon in 1991, where he also spent nine years. He made nearly 300 league games for each club, scoring 77 and 59 goals respectively. He also represented Jamaica on 8 occasions between 1997 and 1998, scoring one international goal. He appeared in the 1998 World Cup, scoring his nation's first ever goal in the finals.