He would have to wait for almost two years until Ajax in the Netherlands hired him on a contract starting from July 1997. He attracted Danish national team captain Michael Laudrup to the club, and together they won the Double of the Eredivisie championship and Dutch Cup trophy as well as reaching the quarter finals in the UEFA Cup. In his second year at the club, tension arose in the Ajax dressing room, as Dutch internationals Ronald de Boer and Frank de Boer boycotted training in order to leave the club in favour of FC Barcelona. As results began to suffer, Olsen was sacked in December 1998.