There was a chance for Winterbottom to erase some of the memories of that defeat when Harlequins looked like beating Bath in the dying minutes of last season's Cup final. Then came that stupendous dropped goal by Stuart Barnes with the last kick of the game.
Then yesterday, a glorious sunny afternoon when everything was right in the world, Winterbottom lost out again. The bold, brave Harlequin - captain this time, playing his last game for his club - tasted defeat once more.
Harlequins led for nearly 50 minutes, but once they fell behind they never looked as though they were going to be able to hold Leicester. The more the game wore on, the more Leicester waxed. When the whistle went more Harlequins were on their knees than were still standing.
One Leicester player who waxed more than most was Neil Back, whose performances have come to seem to be supercharged these past few months, and it was one of the sub-plots of this cup final that pitted Back against Winterbottom. As early as the 15th minute Back was caught in possession. One minute he had the ball in his hand. The next he was moving backwards at a rate of knots, driven by a furious tackler who turned out to be none other than Winterbottom.
There was an edge to that tackle all right. But their styles of play have never been so strikingly similar. Back roams tirelessly often featuring in a move twice. Winterbottom, who hasn't the same pace, is perhaps the more lethal tackler, though there was one tackle late in the game by Back on Gavin Thompson that must have rattled the back teeth of the spectators high in the stand.
A spectator walking to Twickenham on a day such as this was captivated by the sounds of spring. Perhaps it was asking too much that on such a day the game would match the surroundings. There were moments in the second half when it seemed as though both sides simply wanted to get the ball and kick it as far as they could downfield.
Leicester probably didn't mind for they were leading by now, but it is questionable whether it was Harlequins' best tactic.
On such a sunny day something had to give. It was the scoreboard. It coped with recording the England under-21 victory by 31-3 over the French Armed Forces, but it stubbornly refused to yield anything other than an odd line or squiggle for Leicester. At half- time, when Harlequins led 13-10, the scoreboard was showing Harlequins 13 Leicester). Later it adjusted itself to record a score of Harlequins 14 Leicester]
There were 56,165 spectators at the final, a capacity crowd, including 1,765 watching from the executive boxes. The game was a disappointment for all but Leicester's supporters. It never approached the quality of Leicester's semi-final victory over Northampton. But that won't worry the Tigers - it was their seventh final and their fourth victory.
At the final whistle Back turned to the referee Tony Spreadbury, shook his hand and then moved around offering congratulations to Harlequins players. As the pitch disappeared beneath the on- rushing spectators one searched for Winterbottom. But in vain. If he was there he was nearly invisible. Perhaps, instead, he had dashed for the safety of the touchline. And never mind the winter of his discontent; this was the spring of disappointment.