When the giant Dutch keeper arrived from Fulham on a two-year contract in 2005, he felt his stay at Old Trafford would not go much further than that.
Having graced the biggest stage at Ajax and Juventus before joining what was supposed to be a revolution at Fulham that turned out rather differently than he imagined, Van der Sar just relished the chance of starring for a major club once again.
However, in joining fellow veterans Ryan Giggs, Paul Scholes and Gary Neville in committing himself to the Red Devils cause for another year, Van der Sar is now edging towards a testimonial.
"I still believed I was doing enough to play for a bigger team but you need someone to take a gamble, which Sir Alex Ferguson did," the 39-year-old Inside United.
"At the time I was 34 so I didn't expect to be here six years.
"I thought that I would be at United for two years and then maybe go and do something else. Instead I am steadily trying to reach my testimonial."
Although Van der Sar has suffered with injuries this term, and does not feel his form has been as good as in previous years, Ferguson still has faith in the former Holland skipper and Ben Foster, for one, can see no route back to the first-team as long as Van der Sar remains around.
The man himself can offer no explanation for his longevity, other than pointing out life is physically much different for a keeper than the men plying their trade in front of him.
And, once he had a talk with wife Annemarie, who suffered a major illness just before Christmas, Van der Sar's decision was an easy one.
"It was important my wife felt okay with it," he said. "If she had said she would rather go back to Holland then we would have done that.
"But I had made up my mind in December that I would keep playing and join the other old boys, who keep on going.
"My position is not as demanding as Paul and Ryan, who have had to run and tackle a lot.
"But the main thing is we are all still enjoying it."
There may not be too much enjoyment to be gained from Sunday's season finale against Stoke at Old Trafford.
United go into the contest still harbouring hopes of lifting a record 19th league title and becoming the first club in English football history to win four championships on the trot.
However, as they are reliant on lowly Wigan avoiding defeat at Stamford Bridge, where champions-elect Chelsea have failed to win just twice all season, the odds are stacked against them.
It leaves Van der Sar facing the prospect of finishing a runner-up, just as he was in his first season at the club, when United also only had the Carling Cup as a consolation prize.
"It is very strange," he admitted. "In the last three years we have been in command. Now we have to wait.
"It is going to be difficult. We have lost a lot of games this year but we are still in there at the end.
"Hopefully Wigan will have a go for it on Sunday and we will hear some positive news."