On February 24, 2008, Fidel Castro stepped down from his role as Cuba’s president, and Tottenham Hotspur last tasted cup success, winning the League Cup. Seventeen years of disappointment have since passed for Spurs fans, but hope now arises under new manager Ange Postecoglou.
In 2008, Spurs secured their victory at the newly opened Wembley Stadium, overcoming Chelsea after a tumultuous season marred by managerial changes and high expectations. Under Juande Ramos, the team had made significant physical improvements, but key moments during the final defined the match. Didier Drogba put Chelsea ahead with a well-placed free kick, only for Spurs to equalise through a Dimitar Berbatov penalty before Jonathan Woodgate sealed the win 2-1, marking Spurs’ first major trophy in nine years.
However, the success did not signal a return to glory. The ensuing years have been fraught with near misses. Tottenham lost subsequent finals, including a defeat in the League Cup to Manchester United in 2009, and again to Chelsea in 2015. They also saw strong league performances but fell short, finishing as runners-up to Chelsea in the 2016-17 Premier League, despite Harry Kane being the top scorer.
The club’s dramatic Champions League final in 2019 ended in heartbreak as they lost 2-0 to Liverpool. More pain followed, with a League Cup final loss to Manchester City in 2021 occurring under the shadow of Jose Mourinho’s controversial sacking just days before the match.
Yet the narrative may be turning a page. With the recent success of underdog teams in English football, including Newcastle and Crystal Palace, the momentum feels different. Postecoglou’s leadership ignites optimism as Spurs approach another chance at silverware, waiting to see if they can end their long trophy drought. As they strive toward glory, fans remain hopeful that the completion of Postecoglou’s second-year trophy prophecy might finally bring back the celebrations that have eluded them for so long.