Only 3 managers have led Spurs to a cup final in the last 16 seasons:

 

Pochettino: 2015 League Cup, 2019 UCL

Mourinho: 2021 League Cup

Postecoglou: 2025 Europa League Cup

Tottenham Hotspur have had only three managers guide them to a cup final in the past 16 seasons: Ange Postecoglou, Jose Mourinho, and Mauricio Pochettino. Each has left a mark by leading Spurs to major finals, showcasing their ability to compete at the highest level despite the club’s long wait for silverware. 

Mauricio Pochettino was the first of the trio, taking Tottenham to the 2015 League Cup final, where they fell to Chelsea, and later to the 2019 Champions League final, losing to Liverpool in a historic run for the club. His tenure brought Spurs close to glory, raising the team’s profile in European football. Jose Mourinho, known for his trophy winning pedigree, managed Tottenham to the 2021 League Cup final, but they were defeated by Manchester City. His time at Spurs was brief but marked by that final appearance, keeping the club competitive in domestic cups. 

see also: Pollock makes Lions squad as Owen Farrell misses out

Most recently, Ange Postecoglou has steered Tottenham to the 2025 Europa League Cup final. His attacking style and bold approach have reignited hope among fans for a trophy after years of near misses. These three managers stand out in Tottenham’s recent history for reaching cup finals, a testament to their tactical acumen and leadership in high stakes moments.

While Spurs have yet to claim a trophy in these finals, the achievements of Pochettino, Mourinho, and Postecoglou highlight their impact on the club’s journey. Fans remain optimistic that Ange can end the drought and bring silverware back to north London. Who’s ready for more Tottenham magic in the finals? Let’s hear your thoughts!