Dutchman Edwin Van Der Sar was one of the best goalkeepers in the world before he signed for Italian Serie A side Juventus in 1999. Premier League heavyweights Manchester United wanted to sign him before he left Ajax Amsterdam to sign for the Old Lady in a £5m deal. Edwin Van Der Sar made his Juventus debut in the 1-1 draw at home to Reggina thus becoming the first non-Italian in the Juventus goal.

Edwin Van Der Sar was the first-choice goalkeeper at Juventus in his first two seasons at the club as the Old Lady finished second in quick succession in the league. In total, the Dutch shot stopper made 66 appearances in the Italian top flight over the course of his first two seasons as a Juventus player. Carlo Ancelotti was the Juventus manager at the time and they had the best defensive record in the league in each of the first two seasons spent by Edwin Van Der Sar at the club.

Dutch goalkeeper Edwin Van Der Sar was impressed a lot of people with his performances as Juventus won the 1999 UEFA Intertoto Cup as he helped the Old Lady compete for the Italian Serie A title. Van Der Sar was largely at fault for the goal scored by Alessandro Calori via a volley as Perugia beat Juventus on the final day of his first season in Turin. The defeat to Perugia allowed Lazio to overtake Juventus and win the league by a solitary point.

Van Der Sar was generally error-prone in his second season at Juventus. The Old Lady were dumped out of both the Coppa Italia and the UEFA Champions League at the first round stage. Edwin Van Der Sar made a lot of high-profile errors during the course of the season including the one that led to him spilling the shot from Japanese player Hidetoshi Nakata before Italian striker VicenzoMontella scored the rebound to secure a 2-2 draw for AS Roma at the home of Juventus on May 6, 2001. Juventus would finish the season two points behind the eventual champions. Edwin Van Der Sar lost his place in the Juventus team afterwards thanks to the big transfer fee paid to sign Gianlugi Buffon from Parma in the summer of 2001.