After an emotional farewell at Old Trafford on Sunday the retiring 40-year-old will play his final match this weekend when United tackle Barcelona in the Champions League final.
It will be the fifth time he has been involved in such an occasion, a record for a goalkeeper, with his personal statistics standing at two won and two lost.
But the man who lifted the UEFA Cup as a 21-year-old with Ajax is experienced enough to know it is the failures that gnaw at the soul.
And with no way of making amends, it is even more crucial United should emerge victorious.
"You do think more about things you lose than what you win," said the veteran Dutchman.
"When you have won, your medal goes into the cupboard or the safe in the bank.
"But when you lose, you know something has slipped through your fingers. It makes you more determined."
For the man whose penalty save from Nicolas Anelka in the Moscow rain three years ago turned him into a lifelong hero of the Stretford End realises the extreme emotions felt by victors and vanquished.
"If we win I won't want to go home. If I lose I won't want to leave home," he said.
"Maybe it sounds strange but I just wouldn't want to see anyone."
In a sense, Van der Sar's European career has been in extra-time since he joined United in 2005.
At 34, having just completed four years at Fulham, he hardly imagined to spend any more time at the top.
Even at Craven Cottage though, it did cross his mind that he might one day return to the stage he enjoyed so much as a youngster.
"I played a few years at Fulham and remember watching Chelsea's Champions League matches against Bayern Munich and Barcelona and thinking it would be great to be playing those kind of games again," he said.
"Thankfully I have managed to do that at United and it is nice that my final match should be on an occasion such as this."
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