Finally, we come to a trophy! In 2008, during an otherwise very poor reign as Spurs boss, Juande Ramos led Spurs to a memorable 2-1 victory over Avram Grant's big-spending Chelsea side at Wembley. Very few people expected the club to emerge victorious from the match, as Chelsea fielded superstars like Petr Cech, John Terry, Frank Lampard, Michael Essien and Didier Drogba in their playing primes. When Drogba struck to give Chelsea the lead after 39 minutes, that opinion certainly didn't change and Chelsea went in at half time a goal to the good. However, Spurs struck back through a seventieth minute Dimitar Berbatov penalty to take the game to extra time - and Jonathan Woodgate rose above the Chelsea defence after 94 minutes to give Spurs the lead. They held on to win their first - and only - trophy of the new millennium.