Born in Arnhem, Gelderland, Van der Meyde signed for AFC Ajax as a youngster, and made his first-team debut aged just 18, helping to a 1–0 win against FC Twente on 12 November 1997. In 1999, in order to gain experience, he was loaned to Twente for one season, and was an undisputed starter for a side that finished sixth in the Eredivisie. It would be in 2001–02 that Van der Meyde established himself as first-choice at Ajax. After a turbulent start, Ronald Koeman was instated as head coach, and the player became an integral part in the rebuilding of the team, making the right-winger position his own. The campaign ended in huge success as the Amsterdam club conquered the double, with him scoring five times in the league. In 2002–03 Van der Meyde – playing alongside the likes of youngsters as Mido, Zlatan Ibrahimović, Rafael van der Vaart, Wesley Sneijder, Steven Pienaar and Cristian Chivu – scored a career-best 11 goals, while also helping Ajax to the quarterfinals in the UEFA Champions League, netting in a crucial 1–1 away draw against A.S. Roma which certified the team’s qualification for the knockout stages.