Born in Bolands,[1] Gregory was named Most Valuable Player of the 1999 season at the Antigua Football Association's Hall of Fame induction.
in March 2001 to embark a career in professional football, whilst completing his secondary education.
[10] He was to return to York City for additional trials before the end of August,[11] but went to play for San Juan Jabloteh for the remainder of their season.
[13] He joined Montreal Impact in the USL First Division in August 2008,[14] but left in January 2009 to rejoin Freemansville.
[1] He was joint seventh top scorer of the 2007 CONCACAF Gold Cup Qualifying with two goals.