A striker, he played for several clubs in the Football League
Born in Ndola, Zambia, Gregory began his career as an apprentice with Ipswich Town, turning professional
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
Neil 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