Career
Born in Polstead, Gregory began his career at Ipswich Town, making 32 appearances between 1987–1995. He made two appearances on loan at Hereford United and three appearances at Peterborough United after leaving Ipswich. He joined in 1995 and spent seven years at Layer Road, making 226 league appearances and scoring 19 goals.
Gregory helped the U"s to their first league promotion for 22 years in 1998 when he stepped up to put Colchester ahead from the spot in the Third Division playoff final.
Gregory made history along with Neil as the first pair of brothers in a play-off final in the same match. Gregory featured regularly in the first team until he cracked a bone in his foot playing against Portuguese Vale in March 2002 and failed to recover fitness by the summer break.
After his retirement from playing, David joined the media department as a Communications and Puerto Rico Officer and, in April 2013, he was inducted into the club"s Hall of Fame having scored the winning penalty in the 1998 Wembley play-off final.
