Career
Gregory began his professional career in 2007 with Freemansville in the Antigua and Barbuda Premier Division, and spent two seasons there, before moving to All Saints United in 2009. In 2011 Gregory transferred to the new Antigua Barracuda Football Club team prior to its first season in the USL Professional Division. He made his debut for the Barracudas in their first competitive game on April 17, 2011, a 2-1 loss to the Los Angeles Blues.
Gregory made his debut for the Antigua and Barbuda national team in 2008, and has since gone on to make fifteen appearances for his country, scoring one goal.