The team won the Second Division in 1989–90 after the signings of Gordon Strachan who became captain, hardman Vinnie Jones (who Wilkinson guided to a whole season with only three yellow cards), Mel Sterland, Chris Fairclough and Lee Chapman.
Wilkinson was instrumental in the opening of Leeds' first modern academy and training facility at Thorp Arch in 1994 known as The Grange, named after Barcelona's La Masia, translated in English as The Farmhouse.
Wilkinson's plans for Leeds were never fully realised however he later applied this blueprint to the national game when implementing the Academy System as FA technical director.
[8] In December 1999, Wilkinson revealed that Arsenal had made an approach for him during the summer of 1995, when they were searching for a successor to George Graham, who had been sacked for accepting an illegal payment three years earlier.
[10] Four months after leaving Leeds, in January 1997, Wilkinson was hired by the sport's governing body in England, the Football Association, to act as its Technical Director, overseeing coaching and other training programmes at all levels of the game.
Wilkinson based the plans for the National Football Centre on the French system at Clairefontaine which nurtured the 1998 World Cup and 2000 European Championship winners.
[2] In his position as Technical Director of the FA, he managed the England team on a caretaker basis in 1999 for a friendly against France following the sacking of Glenn Hoddle.
Following this he acted for a time as the permanent coach of the England under-21 team, controversially selecting himself to replace Hoddle's choice of manager, Peter Taylor.
He returned to the role of caretaker of the senior team in October 2000 following the resignation of Hoddle's permanent successor Kevin Keegan, overseeing a 0–0 draw in a World Cup qualifying match against Finland.
In October 2002, he left his role as FA Technical Director in order to return to club management at relegation threatened Premier League side Sunderland, with Steve Cotterill as his assistant.
He won two league games out of a possible twenty with his worst moment being a 3–1 home defeat to Charlton Athletic on 1 February 2003 during which Sunderland scored three own goals within seven minutes.
[15][16] Wilkinson briefly returned to management in March 2004, taking charge of Chinese club Shanghai Shenhua on a short-term contract, but left two months later for personal reasons.
Notably, Wilkinson's primary function in his role was to negotiate the essential investment that Wednesday required to avoid the threat of administration, when a winding up petition was to be presented by HMRC on 17 November 2010.
Wilkinson was appointed Officer of the Order of the British Empire (OBE) in the 2024 New Year Honours for services to association football and charity.
Wilkinson was also a PE teacher at Abbeydale Grange school, Sheffield, whilst playing semi-professional football for Boston United.