1998–99 AFC Ajax season

During the 1998–99 Dutch football season, AFC Ajax competed in the Eredivisie.

Season summary
Having waltzed to the title during the previous season, Ajax suffered a complete collapse this season to finish 6th, 23 points adrift of champions Feyenoord. This was the club's lowest finish since 1965. The club also suffered poor form in Europe, finishing bottom of their Champions League group stage. Manager Morten Olsen had paid for the club's poor form in December with his job; his replacement, promoted reserve-team coach Jan Wouters, was unable to reverse the team's fortunes but managed to lead Ajax to win the KNVB Cup.

In

 * 🇧🇷 Wamberto - 🇧🇪 Standard Liège, August
 * Georgi Kinkladze - 🏴󠁧󠁢󠁥󠁮󠁧󠁿 Manchester City, £5,000,000
 * Jesper Grønkjær - AaB, £3,500,000, July

Out

 * Edwin van der Sar - 🇮🇹 Juventus, approx. £5,000,000
 * Ronald de Boer - 🇪🇸 Barcelona
 * 🇦🇷 Mariano Juan - 🇦🇷 Racing, loan
 * Michael Laudrup - retired
 * 🇷🇺 Andriy Demchenko - 🇺🇦 FC Metalurh Zaporizhya