[citation needed] He played for Gloucester Primary Schools alongside future Torquay United teammate Wayne Thomas.
He played another 30 times for Torquay, including the 1997–98 play-off final due to regular keeper Ken Veysey being suspended, before moving to Crystal Palace in October 1998 for a fee of £400,000.
He began the 2008 season as first choice keeper and firmly claimed the number one spot as his own with some vastly improved performances including a dramatic equalising injury time headed goal against Cobh Ramblers.
Gregg left Dundalk by mutual agreement on 24 June 2010, citing lack of first team football as the main reason for his departure.
He then decided to hang up the Gloves (despite numerous offers) to concentrate on his Goalkeeper Coaching Career with Just4Keepers, where he has helped several young keepers achieve their dream of becoming professionals.