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

Tottenham Hotspur is one of England’s oldest and history-filled football clubs in the English Premier League. They have tasted many triumphs and achievements in its glorious history. However, in the past few years, they have struggled to get their hands on the major silverware. Spurs have produced some of the finest and most elegant football players over the years such as Luka Modric, Gareth Bale, Harry Kane, Heung Min-Son, and more, who have donned their jerseys for many years. Their last silverware came back in the 2007-08 season, when they won the League Cup (Carabao Cup).

Tottenham Hotspur League Cup Victory

The League Cup final was played between the Chelsea and Tottenham Hotspur on February 24, 2008, at the legendary Wembley Stadium. The Blues were coming to this game as the favorites to lift the trophy but Spurs had some other plans. Chelsea striker, Didier Drogba opened the scoring from the free kick in the first half.

Juande Ramos’ led Tottenham Hotspur returned to the field more motivated and spirited. Wayne Bridge gifted them a penalty when he handled the ball inside the box which Dimitar Berbatov converted and leveled the score 1-1. The game went into extra time as both teams were unable to score the tiebreaker. Jonathan Woodgate scored the winning goal for the Spurs in the extra time, thanks to Chelsea goalkeeper Petr Cech’s mistake.

Spurs haven’t won any silverware since then, although they did manage to reach a few cup finals but couldn’t get their hands on it unfortunately. They came close to lifting the League Cup in 2015 and 2021 but were defeated by Chelsea and Manchester City in the finals.

But the biggest regret for them to this date will be their 2018-19 UEFA Champions League final defeat to Liverpool. The Reds thrashed them 2-0 thanks to the goal from their star players Mohamed Salah and Origi. Still, they had a terrific run to the finals under Mauricio Pochettino.