Sir Alex Ferguson regards himself as hugely fortunate to have worked with two of the best goalkeepers ever - but he hopes to do better replacing Edwin van der Sar than he did finding someone to take over from Peter Schmeichel.
Van der Sar confirmed yesterday that he will retire from football at the end of the season.
Although the 40-year-old is still producing high-class performances, he is keen to bow out at the top and believes extending himself into another arduous campaign would be too much.
It means Ferguson is now beginning a search for the Dutchman's successor, just as he did in 1999 when Schmeichel headed off for Sporting Lisbon.
On that occasion, the United boss made a big mistake in not signing Van der Sar from Ajax.
It triggered a tortuous six years at Old Trafford, when 10 keepers tried and failed to fill Schmeichel's enormous gloves before Van der Sar headed north from Fulham.
"We hope we are better organised about it this time," said Ferguson.
"There will always be a comparison between Peter and Edwin.
"In my time those two were the outstanding goalkeepers, not just at our club, but in their entire careers.
"Look at the rich career that Edwin had; four Champions League finals, three World Cups. It was fantastic and Peter, of course, was recognised by everyone at the time as the best goalkeeper in the world.
"They are different personalities. But they are great characters and I have been very fortunate to have the two of them."
Having initially signed Van der Sar on a two-year contract, Ferguson could hardly have expected to retain such vast experience for six seasons.
It has coincided with one of the most productive periods in United's history, including three successive Premier League titles and a Champions League triumph in addition to one losing final and another semi-final appearance.
"Edwin's impact as a professional is the one thing I will always remember about him," said Ferguson.
"He has been absolutely fantastic in all areas, quite apart aside from his ability on the football field. His training performances, his example to young players, his personality in the dressing room. He is a really special man.
"But he made the point himself, it is pointless trying to be superman into your 40s. There has to be a time for everyone in football.
"It is one of the sad parts of my job that you get to the stage where age takes over."
As speculation intensifies about who might arrive as the new number one - Germany's Manuel Neuer, Maarten Stekelenburg of Holland, France's Hugo Lloris and current Russia number one Igor Akinfeev are just four of the many names being mentioned - Anders Lindegaard may get his first opportunity to stake a claim at Southampton tomorrow.
Lindegaard is yet to play a competitive game for United since his arrival from Aalesunds but with Van der Sar sitting out the trip to the south coast in order to be fresh for Tuesday's Premier League encounter, he may get his chance ahead of Tomasz Kuszczak.
Van der Sar's decision does bring certainty to his career, just as Ryan Giggs has done by confirming he will carry on for another year.
Gary Neville has not spoken about his own future, although it seems highly unlikely he will carry on.
However, Paul Scholes is yet to make up his mind, even though Ferguson has already asked him to play for an extra year.
"Paul has not made up his mind," said Ferguson.
"I hope he stays on for another year. I think he can do that but I will leave it with him."