As the deadline for moves came and went yesterday, the Elland Road manager was heading for a treble. If Blackburn win the Premiership this season, an increasingly likely prospect, then Wilkinson's business dealings will have played a large part in deciding the destination of the championship for three successive seasons.
His buying and selling of Eric Cantona helped win the title for Leeds and Manchester United in 1992 and 1993 while the decision to let David Batty go to Blackburn for pounds 2.75m is taking on the appearance of the turning point of this season.
Even now the fee seems inflated for a midfield player whose distribution at Leeds never matched his more destructive skills but it would be facile to deny his effect at Blackburn. Batty, free from the burden of being 'the next Billy Bremner', has blossomed into a creative force at Ewood Park, forming a central midfield partnership with Tim Sherwood that only the Old Trafford pairing of Paul Ince and Roy Keane compares with.
Just three League matches have been lost since Batty has been at Blackburn which has whittled United's lead, once 15 points, to six points. And what will pounds 2.75m be to Jack Walker if he has the Premiership trophy as a trinket to adorn his steel fortune?.
Blackburn, too, would lay claim to the best buy of the year had Graeme Le Saux been purchased the day after the transfer deadline last season instead of on it. Twelve months ago Le Saux was a bit player with an ill- defined role in an ill-defined Chelsea team, now he is England's left-back. At pounds 675,000 that represents value that has not always been a hallmark of Kenny Dalglish's dealings.
With Le Saux ineligible, the choice of the most inspired piece of business is not clear cut. Peter Beardsley ( pounds 1.4m) has elevated Newcastle to third place in the Premiership while Andy Pearce ( pounds 500,000) has been far from outshadowed by Sheffield Wednesday's other expensive defensive purchase, Des Walker. Honourable mention, too, should go to Trevor Sinclair at QPR and David Rocastle at Manchester City.
It is at the lower end of the market that true value has been achieved, however. The purchase of Rick Holden for pounds 450,000 from Manchester City has taken Oldham to the FA Cup semi-finals if not Premiership safety while the pounds 150,000 (plus appearance increments) Wolves spent on Chris Marsden in January may yet prove to be the recently departed Graham Turner's most valuable legacy to his successor.
Arguably the best buy of all cost nothing, however. Alan Harper has spent a career being underrated at Everton, Sheffield Wednesday and Manchester City and his work goes unnoticed for much of the time at Luton now. He and Kerry Dixon are the old heads from whom David Pleat's younger players are gleaning wisdom, however. 'Old dogs teaching the pups,' as the manager puts it. An FA Cup semi-final place suggests they are learning fast.
As for the worst buys of 1993-94, every supporter could name a player at his club who has failed to live up to expectations but this season there have been some colossal under- achievement. Alan Kernaghan, pounds 1.5m from Middlesbrough, will probably be the name Brian Horton will take to the grave of his Manchester City managership while Leeds supporters get almost as animated on the subject of Brian Deane's pounds 2.9m fee as they do on the selling of Cantona and Batty.
The most costly mistakes came at Anfield, however, where the flounderings of Graeme Souness's expensive purchases were paid for with his job. To let Beardsley go three years too early was bad enough, but there was also a long list of bad buys, the last of which is Nigel Clough ( pounds 2.25m) who arrived as the new Dalglish but now cannot reach the status of a latter-day David Fairclough as he is not even on the substitutes' bench.
THE SEASON'S TOP TRANSFERS
Roy Keane (Nottingham Forest to Manchester United) pounds 3.75m
Brian Deane (Sheff Utd to Leeds) pounds 2.9m David Batty (Leeds to Blackburn) pounds 2.75m
Darren Peacock (QPR to Newcastle) pounds 2.75m
Andy Sinton (QPR to Sheff Wed) pounds 2.7m
Des Walker (Sampdoria to Sheff Wed) pounds 2.7m
Paul Warhurst (Sheff Wed to Blackburn) pounds 2.7m
Neil Ruddock (Tottenham to Liverpool) pounds 2.5m
Tim Flowers (Southampton to Blackburn) pounds 2.4m
Nigel Clough (Nottm Forest to Liverpool) pounds 2.275m
Ruel Fox (Norwich to Newcastle) pounds 2.25m Andy Townsend (Chelsea to Aston Villa) pounds 2.1m
David Rocastle (Leeds to Manchester City) pounds 2m
David White (Man City to Leeds) pounds 2m