Tottenham’s Trophy Drought: A Look at the Curse

Where Are Tottenham Hotspur Falling Short in the Trophy Hunt?

Thursday, March 20, 2025

For nearly two decades, Tottenham Hotspur has struggled to claim silverware, despite the club's reputation as one of the most competitive sides in English football. The last time Spurs lifted a major trophy was in 2008 when they secured the Carabao Cup. Since then, their pursuit of success has been marred by near misses and managerial changes, with even renowned trophy-winning coaches such as Antonio Conte and Jose Mourinho failing to break the club’s title drought.

The Trophy Curse at Spurs

A recurring pattern has emerged: players who leave Tottenham often find success elsewhere, winning trophies with new clubs. A recent example is Kieran Trippier, who secured his second major title since departing Spurs by helping Newcastle United defeat Liverpool in the Carabao Cup final last Sunday.

However, for former Spurs talisman Harry Kane, the wait continues. Now at Bayern Munich, he could finally put an end to his trophy drought, with his team leading the Bundesliga by six points ahead of Bayer Leverkusen.

Notably, this trend excludes players who won titles while out on loan, such as Bryan Gil and Giovani Lo Celso. The sheer volume of ex-Spurs players winning elsewhere, however, raises serious questions about the club’s ability to convert potential into success.

The Long List of Spurs Alumni Who Have Won Titles

Since leaving Tottenham, 44 players have gone on to secure silverware at other clubs. Here’s a look at some of the most notable achievements:

• Luka Modric: Four-time La Liga champion and six-time UEFA Champions League winner with Real Madrid.

• Kyle Walker: Six-time Premier League winner with Manchester City.

• Kieran Trippier: La Liga winner with Atletico Madrid and Carabao Cup winner with Newcastle United.

• Lucas Moura: Won three titles with São Paulo since returning to Brazil.

• Toby Alderweireld: Secured two titles with Royal Antwerp.

• Jan Vertonghen: Won the Primeira Liga with Benfica.

• Christian Eriksen: FA Cup and Carabao Cup winner with Manchester United.

• Davinson Sanchez, Tanguy Ndombele, Carlos Vinicius: Super Lig winners with Galatasaray.

• Erik Lamela, Etienne Capoue, Juan Foyth: Europa League winners with Sevilla and Villarreal.

• Vedran Corluka, Roman Pavlyuchenko: Domestic league winners with Lokomotiv Moscow.

• Rafael van der Vaart: Superliga winner with FC Midtjylland.

• Joe Hart, Cameron Carter-Vickers: Multiple-time Scottish league winners with Celtic.

• DeAndre Yedlin: Championship winner with Newcastle United and League Cup winner with Inter Miami.

• Paulinho: Title winner with Barcelona and Guangzhou Evergrande.

• Harry Winks: Championship winner with Leicester City.

• Georges-Kevin Nkoudou: Turkish Super Lig winner with Besiktas.

• Fernando Llorente: Coppa Italia winner with Napoli.

• Vincent Janssen: League title winner with Monterrey and Royal Antwerp.

• Paulo Gazzaniga, Josh Onomah: Championship winners with Fulham.

• Benjamin Stambouli: Ligue 1 winner with PSG.

• Kevin-Prince Boateng: Titles with AC Milan, Eintracht Frankfurt, and Barcelona.

• Clint Dempsey: MLS Cup winner with Seattle Sounders.

• Steven Pienaar: South African league winner.

• Vlad Chiriches: Three-time Romanian league winner with FCSB.

• Pierluigi Gollini: Serie A winner with Napoli.

• Adam Smith: Championship winner with Bournemouth.

• Zeki Fryers: League Two winner with Swindon Town.

• Fraizer Campbell: Championship winner with Cardiff City.

• Jimmy Walker: National League winner with Lincoln City.

• Hossam Ghaly: CAF Champions League winner with Al Ahly.

• Paul-Jose M’Poku: Belgian Cup winner with Standard Liège.

• Tomislav Gomelt: Romanian Cup winner with CFR Cluj.

• Simon Dawkins: MLS Cup winner with San Jose Earthquakes.

• Tomas Pekhart: League champion with AEK Athens, Hapoel Be’er Sheva, and Legia Warsaw.

• Bongani Khumalo: Multiple domestic trophies in South Africa.

• Nathan Oduwa: League and cup champion with Olimpija Ljubljana.

• Tom Glover: Three-time title winner with Melbourne City.

Why Can’t Spurs Win?

Despite boasting talent, financial backing, and world-class managers, Tottenham has failed to establish a winning culture. The inability to capitalize on crucial moments and sustain high-level performances throughout the season has cost them dearly. Many fans and analysts point to inconsistent squad depth, managerial instability, and a mental block in high-stakes situations as key issues.

As another season nears its conclusion, the question remains: when will Tottenham Hotspur finally break their trophy drought?