Each presided over successful, sometimes trophy-laden, periods in the club’s history and subsequently have been honoured by the club and its supporters.
Wilkinson led the Whites to the 1990 Second Division title, followed by First Division glory two seasons after in a remarkable rise back to the forefront of English football, which would scarcely be achievable nowadays.
Affectionately known as ‘Sgt Wilko’ by the club’s fans, Wilkinson still retains a special place in the hearts of those who count themselves as Leeds supporters.
Wilkinson’s influence on young players at Leeds is best measured by the recent success enjoyed at the club’s Thorp Arch academy facility which was founded in 1994 as ‘The Grange’.
Some 16 years after it was established, a young Kalvin Phillips walked through the doors at Thorp Arch and never looked back, made possible due to Wilkinson’s focus on player development almost two decades earlier.
Here are some of the best and most iconic images of Wilkinson’s reign at Leeds and beyond during the 1990s.
1. 8 May 1990: Leeds United manager Howard Wilkinson lifts the Division Two Championship trophy
8 May 1990: Leeds United manager Howard Wilkinson lifts the Division Two Championship trophy after victory in the match against Bournemouth at Dean Court in Bournemouth, England. \ Credit: Dan Smith /Allsport Photo: Dan Smith
2. Howard Wilkinson before the beginning of the 1991/92 season
1991: HOWARD WILKINSON, THE MANAGER OF LEEDS UNITED SOCCER CLUB, DURING A CLUB PHOTOCALL BEFORE THE START OF THE 1991/2 SOCCER SEASON. Mandatory Credit: Allsport UK/ALLSPORT Photo: Getty Images
3. Howard Wilkinson issues instructions from the bench en route to First Division glory during 1991/92
Leeds v Crystal Palace 23-3-91 Howard wilkinson issues instructions from the bench Photo: Varley Picture Agency
4. First Division title winners
Leeds United captain Gordon Strachan (4th left front row) and manager Howard Wilkinson (left front row) celebrate First Division glory at Elland Road on May 2, 1992 in Leeds, England. (Photo by Getty Images/Getty Images) Photo: Getty Images
5. Howard Wilkinson and Carl Shutt after defeating Stuttgart in Barcelona
1992: Howard Wilkinson (left) Manager of Leeds and Carl Shutt (right) of Leeds celebrate after winning the European Cup first round replay match against Stuttgart in Barcelona, Spain. Leeds won the match 2-1. \ Mandatory Credit: Allsport UK /Allsport Photo: Getty Images
6. Howard Wilkinson shakes hands with Tomas Brolin - a £4.5 million signing from Parma. Not Leeds' most successful record buy
17 NOV 1995: TOMAS BROLIN SIGNS FOR LEEDS UNITED FOOTBALL CLUB FOR A RECORD FOUR AND A HALF MILLION POUNDS SEEN HERE WITH BILL FOTHERBY MANAGING DIRECTOR AND HOWARD WILKINSON LEEDS TEAM MANAGER Mandatory Credit: Allsport UK/ALLSPORT Photo: Getty Images