Following his release from Crystal 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 making 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 he saved a penalty in the shoot out it wasn’t enough to stop Brackley Town lifting the trophy.
On Joining the Wood Gaffer Luke Garrard said ” I am delighted to have secured David’s signature. He comes to us having spent the last two years with Bromley making more than 90 appearances over that period. During his time there he was a pivotal player who was instrumental in Bromley reaching the FA Trophy final in 2018 and competing for a play-off place both seasons.”
Garrard continued, “David will add real competition for places in the goalkeeper department and work alongside England C goalkeeper Ryan Huddart and new goalkeeping coach Martin Brennan, so I am excited that all three will create an excellent environment for both to develop.”