Gregory started his career at Crystal Palace spending over a decade with the Eagles. During his time at Palace Gregory was loaned out to Leyton Orient.
Following his release from Palace in 2016, he joined Cambridge United, then managed by Shaun Derry. Due to the form of Will Norris, Gregory’s appearances for Cambridge were limited, as he made just one league appearance.
Gregory then joined Neil Smith at Bromley, making himself a firm fans favourite. In his first season with the Ravens, he kept an impressive 20 clean sheets. He also went on to play at Wembley in the FA Trophy Final, and although saving a penalty in the shootout, it wasn’t enough to stop Brackley Town lifting the trophy.