2010: After signing with the English club Forrest Green Rovers to stay match fit, he signed a contract with KC in March and started 18 games among his 23 appearances. He recorded three assists, playing primarily in the midfield. Also started in Kansas City’s 2-1 win over Manchester United during summer friendly and played full 90 in U.S. Open Cup play-in match against Colorado.
2009: Joined Forest Green Rovers, making 13 appearances in the Conference National league in England.
2008-2009: Played in 13 games for Thrasivoulos Filis in the Greek Super League.
2007-2008: Signed with Port Vale, for whom he made 23 appearances and scored a goal before being loaned out to Gillingham for the remainder of the season.
2006-2007: Moved to Oldham Athletic, making 35 appearances and scoring two goals.
2005-2006: Made 28 appearances, scoring one goal for Sheffield Wednesday before appearing eight times for Yeovil Town on loan.
2003-2005: Transferred to English giants Chelsea, spending time on loan at Barnsley, Lincoln City, and Hibernian.
2001-2003: Appeared in 28 games for Kingstonian FC in England's Isthmian League.
Rocastle made his international debut for Grenada in a 1-1 draw against Martinique at the 2010 Digicel Caribbean Cup. Played all five matches in tournament as Grenada qualified for 2011 CONCACAF Gold Cup.
Owns one male pug. Likes seeing new movies in the theater with his wife. Also enjoys bowling and playing Nintendo Wii. Has one sibling, an older sister.