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.
[10] He appeared in further twelve minutes in a 2–1 away success against Stevenage in the Football League Cup two days later,[11] and featured on the bench in a 1–1 home draw against Reading on 14 August.
[16] 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 USA in October.
[22] In 2018, Gregory returned to America to sign for National Premier Soccer League side Orange County and he continued to play for the club in the 2019 season too.
[24] After a break from the game, Gregory signed for Whitehawk in November 2021, playing under Ross Standen, assistant manager from his Lewes days,[25] before leaving at the end of the season.