The Dutchman made a name for himself at Ajax where he helped the club win four consecutive Eredivisie titles and the Uefa Cup.
After nine years in his homeland Van der Sar was starting to attract interest from across Europe.
Despite the goalkeeper opting to join Juventus in 1999, Van der Sar came close to sealing a move to Anfield and even travelled to Merseyside to meet manager Gerard Houllier.
Van der Sar, who became a Manchester United hero during his six-year spell at Old Trafford, even seemed to take a dig at his rivals Liverpool when explaining what happened – stating he saw Juventus as a bigger challenge than the Reds despite Juve dominating Serie A at the time.
“When I left Ajax in 1999, I travelled to Liverpool and spoke to Houllier,” Van der Sar told FourFourTwo.
“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.”
Van der Sar’s decision to join Juve saw him win only the Uefa Intertoto Cup during his time in Italy before he moved to England.
After four seasons with Fulham, Van der Sar sealed a move to United and went onto win four Premier League titles and the Champions League under Sir Alex Ferguson.