Each time, first against Blackburn and then at the hands of Swindon, the outcome of 10 months' hard slog hinged on a dubious penalty decision against Leicester in the Wembley final. Both were converted, making it all the more surprising that Little is too.
The Leicester manager's support for the system is based on its success in keeping the season alive for so many clubs. He points to the interest of spectators in what were once 'dead' games during February and March. The revenue generated - 150,000 watched last year's three divisional finals at Wembley - also assuages objections to using a cup-tie format to resolve league issues.
Swindon's subsequent demise in the Premiership has underlined the chasm in class that those seeking elevation by the back door must attempt to overcome. That, however, is a problem with which all the managers whose teams are involved in tomorrow's semi-final first-leg matches would willingly grapple.
Strange how certain names keep cropping up in this annual festival of frayed nerves. Only four of the 12 clubs taking part do not qualify for the legend 'Gluttons for Punishment' to be embroidered beneath their club crests. Indeed, Tranmere and Stockport are competing in the play-offs for the fourth time in the eight seasons since their inception, equalling Blackburn's record.
Tranmere and Leicester, who collide on Merseyside, should therefore have a good idea of the tactical approach necessary. Conventional wisdom claims that playing the second leg at home - as the side finishing higher are allowed to do - is a distinct advantage. But the records offer no such encouragement to Little, revealing only a 50 per cent success rate for the club staging the return.
The two League games between them suggests an extremely tight contest, Tranmere having won 1-0 at Prenton Park before drawing at Filbert Street. By the same criteria, the other First Division semi-final is even more finely balanced. Derby and Millwall, who commence hostilities at the Baseball Ground, fought out two 0-0 draws.
Derby, who alone appear equipped financially to avoid Swindon's fate, have the personnel to make sure of succeeding where they failed against Blackburn in 1992. In Paul Kitson, Tommy Johnson and Marco Gabbiadini, not to mention Craig Short at set-pieces, they have more potential match-winners than any of their rivals. The question now is whether Roy McFarland's men also possess the mental strength.
Burnley and Plymouth, both of whom could definitely sustain a higher level of football, should play before a capacity crowd at Turf Moor. With only four away wins all season, Burnley would be advised to make the most of tomorrow's match.
Curiously, given that Marlon Beresford and Alan Nicholls are two of the best goalkeepers outside the Premiership, the teams' Second Division encounters produced 11 goals.
York, guided by Brian Little's younger brother, Alan, may have the edge in sharpness over Stockport. Having won last year's Third Division final after a shoot-out, York have been playing without the attritional effects of chasing automatic promotion, which Stockport narrowly missed.
It is a measure of the expectations raised by Martin O'Neill at Wycombe that last season's Vauxhall Conference champions will be disappointed at having to repeat the 600-mile round trip to Carlisle with which they started League life.
Michael Knighton, the Carlisle chairman, who might have been taking the acclaim at Wembley today had things worked out with Manchester United, is confident he will be watching his new club play beneath the twin towers a fortnight today. And if Preston see off Torquay to set up the nearest the Cumbrians come to a derby, so much the better.