Career
Early career
Born in Eastbourne, Gregory started his footballing career at Brighton"s youth setup before moving to Portsmouth Academy. After being offered a scholarship deal with the latter in June 2008, he was a regular first choice in the Premiership Reserve League. Portsmouth
Gregory signed a one-year professional deal with Portsmouth on 1 July 2010, being assigned number 39.
He played in pre-season matches against Fulham and Bournemouth, and was also taken on the club"s North American Tour playing against Club America, District of Columbia United, Football Club Edmonton and Ventura County Fusion.
Gregory made his first team debut on 7 August, replacing John Utaka in the 83rd minute of a 0–2 Championship away loss against Coventry City. He appeared in further twelve minutes in a 2–1 away success against Stevenage for the Football League Cup two days later, and featured on the bench in a 1–1 home draw against Reading on 14 August.
Gregory made no further appearances for Pompey during the campaign, and was released along with nine players on 15 May 2011. Eastbourne/Lewes
On 15 November, Gregory signed a contract with Eastbourne Borough.
However, after being sparingly used, he joined Lewes in March 2012.
Gregory played in ten matches for the Rooks during the season, all as a starter. Nottingham Forest
On 27 September Gregory left Lewes and joined Nottingham Forest. After playing regularly with the U21"s, he was released in May of the following year.
Trial periods
Shortly after being released, Gregory moved abroad for the first time in his career, joining Hansa Rostock in a trial basis.
In January of the following year he was selected for the North American Soccer League Combine at the University of California, after training for a couple of days with Chivas United States of America in October. In March 2014 Gregory had a trial at Charlton, but nothing came of lieutenant
Ventura County Fusion
In May 2014 Gregory joined USL Premier Development League side Ventura County Fusion. Beira-March
On 12 July 2014 Gregory switched teams and countries again, signing a one-year deal with South Carolina (U.S.) Beira-March
He made his debut for the club on 17 August, replacing Bilal Sebaihi in the 78th minute of a 0–1 away loss against Oriental for the Segunda Liga championship.
On 11 December 2014, Gregory announced on his official site that he had left the club