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. In the inaugural Premier League season of 1992–93, Shipperley made his professional debut towards the end of the campaign. 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. Shipperley was signed for Southampton by Alan Ball for a record fee of £1.25 million on 6 January 1995. New manager Graeme Souness signed Norwegian Egil Østenstad, prompting Shipperley to drop to the First Division by signing for Crystal Palace for a £1 million fee in October 1996. He scored 13 times for the Eagles over the rest of the season as the 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. In 1997–98, he scored seven times – including five consecutive games from October to December – in a season that ended with relegation.
Nottingham Forest and Barnsley
In September 1998, Shipperley returned to the Premier League by signing for Nottingham Forest for £1.5 million. He scored only once in 21 games as Forest went down, that coming on 13 March 1999 to round off a 3–1 win at his future club Wimbledon. For 1999–2000, Shipperley signed for First Division club Barnsley for £700,000. 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. 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, though his team would lose 4–2 to Ipswich Town in the final at Wembley.
Wimbledon and return to Palace
Ahead of the 2001–02 season, Shipperley joined Wimbledon for £750,000, and scored on his debut on 11 August to open a 3–1 win over Birmingham. He scored 12 times in his first season with the Dons, including braces in both games against eventual champions Manchester City. He built captained the side, and built a prolific partnership with Irishman David Connolly in 2002–03, the club's final season. In July 2003, Shipperley returned to Palace on a three-year deal. 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.
Later career
After Palace's immediate relegation, Shipperley moved on to Sheffield United on a two-year deal on a free transfer in July 2005. He scored 11 times as the Blades won promotion as runners-up to Reading, including two on 10 December in a 3–0 home win over Burnley. On 15 January 2007, his contract with Sheffield United was terminated by mutual consent, and he signed a four-month contract with Brentford, eight days later. He failed to score in his eleven appearances for Brentford, and on 25 April 2007 announced his retirement from professional football. In June that year, he rejected the chance to play for Wimbledon's successor AFC Wimbledon, telling the Surrey Comet that he was in the Middle East to coach a club there.
Management career
On 20 May 2009, it was announced that Shipperley had become manager of Bedfont in the Combined Counties League. In the summer of 2010, Shipperley was appointed manager of Walton Casuals in the Isthmian League Division One South. After 15 months in the role he quit the club however in October 2011. On Boxing Day 2011, Shipperley was confirmed as the successor to Steve Ringrose at North Greenford United a post he held until May 2012 when he resigned to look for management experience at a higher level, though he returned in October 2012 following the sacking of Jon-Barrie Bates. He made an appearance as a player against Leighton Town in the final game of the 2012–13 season. Shipperley's second spell as manager at Berkeley Fields came to an end when he resigned in February 2014 following a 4–1 defeat to Dunstable Town.
In December 2019, he was found guilty of masturbating in front of a mother and her 16-year-old daughter and was given a 12-month community order, ordered to complete 120 hours' unpaid work and pay a £90 victim surcharge, £85 in costs and £200 in compensation. 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. Shipperley had been receiving counselling for personal issues, including the death of his father and gambling addiction, as well as debts.
