A former youth team player at Queens Park Rangers, in 2001, he joined Kingstonian from Gravesend and Northfleet after a loan spell with Ashford Town (Kent).
Rocastle was with Isthmian League Premier Division club Gravesend and Northfleet when in September 2001 he went on trial to Queens Park Rangers,[3] who during his stay with them went into administration.
After a loan spell in November 2001 with Southern League Eastern Division club Ashford Town (Kent),[4] it was announced in early December 2001 that he had left Gravesend and Northfleet.
Rocastle made his debut in the English Football League on 14 February 2004, at the age of 22, playing for Barnsley in a 1–0 defeat at Wrexham's Racecourse Ground.
In late-March he joined Third Division side Lincoln City on loan,[10][11] but only made two substitute appearances before returning to Stamford Bridge before the end of the season.
[19] He played for the "Owls" in the League One play-off final, which finished as a 4–2 victory over Hartlepool United at the Millennium Stadium in front of close to 60,000 spectators.
Rocastle then joined Crewe Alexandra for a trial,[28] but he failed to win a contract after playing 45 minutes in a pre-season friendly with Nantwich Town.
Following a short trial in March 2010, Rocastle departed Forest Green to sign for Kansas City Wizards in Major League Soccer.
He made his Grenada international debut on 26 November 2010, in a 2010 Caribbean Cup match against Martinique at the Stade d'Honneur de Dillon in Fort-de-France.
[37] He was named by coach Mike Adams in the 2011 CONCACAF Gold Cup at the United States, and played the first half of the 4–0 defeat to Jamaica at The Home Depot Center, before being taken off for Lancaster Joseph.