Notable roles in television and film include EastEnders as Mikey, Samson and Delilah (1996), Octane (2003), Stoned (2005), Green Street (2005), The Mark of Cain (2008), Wild Bill (2011), The Hooligan Factory (2014), and Once Upon a Time in London (2019).
In 1996, Gregory starred in the television miniseries Samson and Delilah (1996) in a cast which included Elizabeth Hurley, Michael Gambon, Dennis Hopper, and Diana Rigg.
[4] In 2002, Gregory played Sam, a lead character in the BBC British young offenders television film Out of Control, alongside Tazmin Outhwaite.
[8] In 2011, he also appeared in Wild Bill, in a cast which included Charlie Creed-Miles, Will Poulter, Neil Maskell, Liz White, Iwan Rheon, Olivia Williams, Jaime Winstone, Andy Serkis, and Sean Pertwee.
[10] In 2019, he starred in the British period gangster film Once Upon a Time in London, alongside Holly Earl and Terry Stone.