After establishing a reputation as one of European football's finest goalkeepers with a trophy-laden nine-year stint at Ajax, the towering Dutchman eventually signed for Juventus in the summer of 1999 and spent two seasons in Turin before the big-money arrival of Gianluigi Buffon led him to depart for Fulham.
In a recent interview with FourFourTwo, Van der Sar explains how he held talks with Liverpool before opting for Serie A and how United's decision to secure the return of Mark Bosnich as a successor to Peter Schmeichel led to a six-year delay in Sir Alex Ferguson finally sealing his signature.
"When I left Ajax in 1999, I travelled to Liverpool and spoke to [manager Gerard] Houllier," he said. "I was shown around Anfield and also met with the chairman and a couple of the players.
"I thought about it, but when Juventus came to the table I came to the conclusion that it would be a bigger challenge to play in Italy."
United struggled badly to replace the hugely influential Schmeichel, of course, with a parade of underwhelming goalkeepers in Bosnich, Massimo Taibi, Raimond van der Gouw, Fabien Barthez, Roy Carroll and Tim Howard all failing to impress before Van der Sar became the first signing of the Malcolm Glazer era in 2005 in a bargain £1.5m ($1.9m) deal.
The ultra-reliable custodian, a veteran of 130 international caps for the Netherlands, went onto make 266 appearances during six seasons under Ferguson before retiring after a Champions League defeat to Barcelona at Wembley Stadium in 2011, keeping a total of 135 clean sheets.
He also added four Premier League titles, another European Cup, two League Cups, one Club World Cup and three Community Shields to his bulging trophy cabinet during that hugely successful span.
Since hanging up his boots, Van der Sar, who still appears for United in testimonials and charity legends matches, has returned to Ajax and served as the Amsterdam outfit's commercial director before being promoted to CEO in December 2016. He recently resigned as their "technical heart", but remains in a general manager capacity.
The 46-year-old briefly came out of retirement last March to play and save a penalty for Dutch fourth-tier amateurs VV Noordwijk after injuries left his first senior club without a goalkeeper.