Stockley began his career as a trainee at Southampton but was unable to break into the first team. He moved to Barnet during the 1996–97 season and went on to make over 200 appearances for the club before moving to Oxford United for a fee of £150,000 prior to the 2001–02 season. Stockley remained at Oxford for just over a season before moving to Colchester United, where he made over 150 appearances before moving on loan to Blackpool late in the 2005–06 season.
After his release from Colchester, Stockley moved to Wycombe Wanderers, prior to the 2006–07 season. He spent the season as the club's regular right back, but he also filled in as centre back and sweeper during tactical changes. He lost his place at right back to Russell Martin in the 2007–08 season but he was used as a left back on many occasions.
Stockley left Wycombe and signed for Port Vale on 21 May 2008, signing a two year deal. He was made Port Vale captain on 28 July 2008. Less than 2 months later he was stripped of the captaincy in favour of Marc Richards.