When Did Tottenham Hotspur Last Win a Significant Piece of Silverware?

Would you believe it if I were to tell you that Tottenham Hotspur last won a silverware, 16 years, and 348 days? Well, pretty much insane given the number of talents they had nurtured over the years from Luka Modric, Gareth Bale, Harry Kane, Heung Min-Son, and more to the world-class managers at the helm, Mauricio Pochettino and Jose Mourinho still struggled to get their hands on any major silverware title. The last trophy that the club won was the League Cup 2007-08 (Carabao Cup) in 2008.

Tottenham Hotspur League Cup Victory

The Iconic Wembley Stadium hosted the League Cup final played between Chelsea and Tottenham Hotspur on February 24, 2008. It was the first major final being played in the all-new Wembley after the old one was demolished. Chelsea reached the final after beating Everton on a 3-1 aggregate meanwhile, Spurs made it after a comfortable win against Arsenal on a 6-2 aggregate.

Chelsea took an early lead in the 39th minute after Didier Drogba scored a free-kick goal. The game was well within the victory margin for Chelsea, but Wayne Bridge handled the ball inside the penalty box which gave Spurs a chance to level the score and Dimitar Berbatov didn’t make any mistake. Three minutes into the extra time, Jonathan Woodgate netted a header from a cross of Jermaine Jenas of a free-kick onto Petr Cech who pushed it straight into the back of the net.

This was their first major silverware after a nine-year drought. It’s not like they weren’t capable of winning in fact they did reach a few finals but unfortunately couldn’t cross the line. But the final that they must still regret to this date will be the one they lost to Liverpool in 2019. The UEFA Champions League final in Madrid was played between two of the most prominent clubs of the English Premier League.