Born in
Ndola,
Zambia, Gregory began his career as an apprentice with
Ipswich Town, turning professional in February 1992. His brother
David was also a professional footballer. He joined
Chesterfield on loan in February 1994, making his league debut for the Spirerites, and joined
Scunthorpe United on loan in March 1995, hitting 7 goals in 10 games. After the success of his loan spell, he returned to Ipswich and began to feature in the first team, though mainly as a substitute (27 of his 45 league appearances for Ipswich Town came this way). In November 1996 he joined
Torquay United on loan, but failed to score in 5 games, and in November 1997 moved to
Peterborough United on loan. He joined
Colchester United on loan in January 1998, with the move being made permanent on 26 March, Colchester paying a club record fee of £50,000. He was a regular for Colchester during the rest of the season, but was allowed to join the
Boston Bulldogs on loan for the summer of 1999. He joined
Canvey Island on loan in December 1999, signing for them on a free transfer on 4 February after scoring 11 times in 53 games for Colchester. In May 2001 he was a member of the Canvey Island side that won the FA Trophy, and was a regular member of the side that won promotion to the
Conference. In 2001, he scored the winning goals in
FA Cup ties against
Wigan Athletic and
Northampton Town. At the time of the cup run, Gregory was reported to be a full-time house husband. He signed a new twelve-month contract with Canvey Island in June 2005. After retiring from playing, he worked as assistant manager of
Whitton United alongside former Ipswich reserves player Gary Thompson during 2008, before becoming manager of Stowupland Falcons in 2011. Gregory left Stowupland Falcons after 5 years in charge. ==Honours==