Philpott began his career with Peterborough United as an apprentice in 1986.
In 1989 he joined Cambridge United and made over 100 appearances for the U's, scoring 23 goals, helping the club to two successive promotions and two FA Cup Quarter Finals.
The biggest move of Philpott's career occurred in 1992 when he was signed by Leicester City for £350,000. In four years at Filbert Street he made 75 appearances, finding the net on three occasions.
Philpott joined Blackpool in 1996 for £75,000, for whom he went on to make 71 appearances and score five goals in his two years at the seaside.
In 1998, Philpott joined Lincoln City on a free transfer. Two years later, he was on the move again, this time to Hull City signing a three contract until 2003.
The midfielder moved into non-league football with Weymouth in 2003. He spent one year with the Terras, before joining his Harrogate Town, where he was also assistant manager. He was caretaker manager for a spell in February 2005 after the departure of John Reed to Stalybridge Celtic.
Signed as a player for Hinckley United in July 2007 and retired from football in 2008, he now is a Licensed Football Agent.