UEFA Super Cup: 1998
The thrilling Cup Winners' Cup triumph over Stuttgart a few months earlier meant we would meet Real Madrid in the European Super Cup following the Spanish side's Champions League final victory over Juventus.
An impressive Chelsea performance saw us win the match 1-0 thanks to Gustavo Poyet's strike with only eight minutes remaining, ensuring we lifted the trophy for the very first time in our history.
In a closely fought contest in Monaco there were chances at both ends. A Madrid side with an array of talent at their disposal including the likes of Raul, Roberto Carlos and Clarence Seedorf went close on a couple of occasions, most notably when French midfielder Christian Karembeu cracked the post with a brilliant free-kick.
The Blues certainly played their part though, and we were also denied by the woodwork when a wonderful Frank Leboeuf effort from the edge of the penalty area rebounded back off the upright with Bodo Illgner stranded.
The breakthrough came in the 82nd minute; after some neat build-up play the ball broke to substitute Poyet on the edge of the box who, in trademark fashion, fired his effort past Illgner to win the trophy for Gianluca Vialli's side.