Shipperley got his break in football at the age of 15, when playing for Spartan League side Brook House in the Middlesex Charity Cup. The tournament's patron, celebrity astrologer Russell Grant, was friends with Chelsea chairman Ken Bates, whose club sent a team to the tournament. Shipperley bettered Chelsea centre-back Frank Sinclair for strength and pace, and was scouted by the club. An article in "The Independent" in January 1994 predicted that Shipperley could become Chelsea's first homegrown star striker since Peter Osgood in the 1960s.