Shipperley got his break in football at the age of 15, when playing for Spartan League side Brook House in the Middlesex Charity Cup.
On 10 April, he came on as a 65th-minute substitute for Robert Fleck in a 1–0 loss at his future club Southampton, and two days later on his first start and first game at Stamford Bridge he scored their last goal in a 4–2 win against Wimbledon.
[4] He scored 13 times for the Eagles over the rest of the season as they were promoted via the play-offs, including one on 10 May in a 3–1 home win over Wolverhampton Wanderers in the first leg of the semi-finals.
[7] He scored 15 times in 46 total games in his first season, including both of a 2–0 home win over South Yorkshire rivals Sheffield United on 6 November.
[6] On 13 May 2000, he opened the scoring in a 4–0 win at Birmingham City in the first leg of the play-off semi-finals,[9] though his team would lose 4–2 to Ipswich Town in the final at Wembley.
[13] On 29 May 2004 at the Millennium Stadium, he captained the side and scored the only goal of a play-off final win against West Ham United to take the Eagles back to the Premier League.
[21] On Boxing Day 2011, Shipperley was confirmed as the successor to Steve Ringrose at North Greenford United[22] a post he held until May 2012 when he resigned[23] to look for management experience at a higher level, though he returned in October 2012 following the sacking of Jon-Barrie Bates.
He was also made subject to a five-year sexual offences notification requirement order and told to report to Hayes police station within three days.