Gregory began his career as a 15-year-old in the youth ranks of Wycombe Wanderers, his highlight being captaining the side in the Berks & Bucks Senior Cup final win over Milton Keynes Dons.

[2] Gregory made his Football League debut for the Chairboys on 6 May 2006, coming on for Matt Bloomfield in the second half in a 2–0 victory against Peterborough United.

At the end of the 2007–08 season, his contract at Wycombe was not extended and Gregory signed for Hayes & Yeading United, for whom he went on to score two crucial goals in the play-off final against Hampton and Richmond Borough on 7 May 2009 as they won promotion to the Conference National.

For this reason it was decided that Gregory should be sent out on loan, and he opted for his former club AFC Wimbledon as soon as he received the request from the Dons first team coach Simon Bassey.

On 10 July 2016, it was announced that Gregory had signed for Hellenic Football League Premier Division side Thame United.