Original Umbro voetbalshirt Chelsea 1998/00

After a solid fourth-place finish coupled with European and League Cup success the previous season, Chelsea really felt that they could challenge for the title this season. Chelsea made more big name signings, including French World Cup winning defender Marcel Desailly from A.C. Milan, Spanish international full-back Albert Ferrer from Barcelona and, in a club-record £5.4 million move, Italian international striker Pierluigi Casiraghi from Lazio. Casiraghi's season and career was cut short by a knee injury, but his compatriot Gianfranco Zola had arguably the best season of his career, leading Chelsea to a serious title challenge, scoring 15 goals in all competitions and setting up many other goals for his teammates.

Ultimately, the European Super Cup, won by beating Europeans champions Real Madrid, was the only trophy that Chelsea had to show for their excellence. Their defence of the now-defunct Cup Winners' Cup ended in the semi-finals, while their title challenge was ended in early May when they just couldn't get the better of Manchester United or Arsenal. Nonetheless, a final third-place finish booked them their first ever UEFA Champions League campaign and was another triumph for their excellent young manager Gianluca Vialli, who, at 35, announced his retirement as a player to concentrate on his managerial duties.