Career
He was caretaker manager of Football League Two side Portsmouth from November 2012 until April 2013 when he took the role on a permanent basis before being sacked by Portsmouth in November 2013. On the 13th December 2013, he was appointed assistant manager at Crawley Town. As a player he was a striker from 1988 until 2005, notably in the Premier League for Aston Villa and Sheffield Wednesday.
Having started his career with non-league Yeovil Town he went on to play in the Football League for Portsmouth, Wolverhampton Wanderers, Watford, Peterborough United, Oxford United and Wycombe Wanderers.
He amassed over 450 appearances throughout his career. Born in Evesham, after leaving the British Army, he joined Waterlooville for the start of the 1987-1988 season where, after two games for the reserves, he was quickly promoted to the first team and became the club"s top goalscorer in the 1987-1988 season.
One of his goals came in the first round proper of the F.A.Cup against Aylesbury United. He then spent a season at Yeovil Town before, in the summer of 1989, he was signed by Portsmouth, where he then spent the majority of his career, scoring 99 times in 173 league appearances, including Pompey"s all-time scoring record of 42 league goals in the 1992-1993 season (48 in all competitions) as the club missed out on automatic promotion to the Premier League on goals scored.
He was known while at Fratton Park as "Corporal Punishment".
Afterwards he played in the Premiership for Aston Villa and Sheffield Wednesday, proving to be very popular at the Owls. He later returned to Portsmouth in 1999, where his seven goals in nine matches helped the club avoid relegation to the third tier. In the 2000-2001 season, his last as a professional, he scored for three different clubs, notching for Peterborough United (against Oldham Athletic), Oxford United (against Swindon Town) and Wycombe Wanderers (against Bristol City).
Whittingham later went on to become player-manager of Newport Isle of Wight, but left them in May 2005 when the club ran into financial difficulties.
He returned to management at AFC Newbury but when that club suffered financial difficulties and the loss of their ground, Whittingham left in June 2006. In August 2006 he took up a coaching role at Eastleigh.
In January 2009, he joined the Portsmouth first-team coaching staff as development coach. He was named joint caretaker manager of Portsmouth together with Stuart Gray on 14 October 2011, when Steve Cotterill left to become manager of Nottingham Forest.
Whittingham once again became caretaker manager of the south coast club following Michael Appleton leaving to take the vacant position at Blackpool, and stayed as caretaker until the club exited administration in April 2013, with his full-time appointing imminent.
On 25 November 2013, Whittingham was relieved from his duties following a meeting with the Portsmouth board. The 2–1 loss to Southend proved to be his last game in charge on the south coast. Whittingham was appointed first team coach at Crawley on Friday 13th December 2013.