Ajax’s 1998/99 season was a turbulent and disappointing one, marking the end of their dominant 1990s era.
Managed by Morten Olsen, the team entered the season as defending Dutch champions and cup winners but struggled with inconsistency, internal conflicts, and the departure of key players like Frank and Ronald de Boer, Edwin van der Sar, and Jari Litmanen.
In the Eredivisie, Ajax finished a disappointing 6th, their lowest position in years, missing out on European qualification. They were eliminated early in the KNVB Cup and exited the UEFA Champions League in the group stage, finishing behind Olympiacos and Croatia Zagreb.
Despite the emergence of young talents like Zlatan Ibrahimović (who joined shortly after) and Andy van der Meyde, the 1998/99 season marked the collapse of Ajax’s mid-’90s dynasty — a year of decline after years of brilliance.