A look at Tottenham bosses who failed to win trophy as Postecoglou ends drought | OneFootball

Ange Postecoglou has guided Tottenham to a first trophy in 17 years with Europa League glory against Manchester United in Bilbao.

Spurs have experienced several near-misses since they enjoyed League Cup success at Wembley in 2008.

Here, the PA news agency takes a look at the coaches who tried and failed to achieve what Postecoglou has at Tottenham.

Harry Redknapp

Redknapp replaced Juande Ramos, who led Spurs to Carling Cup glory in 2008. Even though Redknapp’s team made the final again the following year, a shoot-out defeat to Man United was the closest the popular English boss would go to winning silverware during four years in north London despite several exciting cup runs.

Andre Villas-Boas

A Gareth Bale-inspired Tottenham made the Europa League quarter-finals under Villas-Boas in 2013, but the former Chelsea boss left after only 18 months and short-term replacement Tim Sherwood could only emulate a last-eight run in Europe before his tenure concluded.

Mauricio Pochettino

Pochettino came closest to the holy grail during a largely successful five years as Spurs head coach with a League Cup final defeat to Chelsea at Wembley in 2015 followed four years later by Champions League heartbreak in Madrid to domestic rivals Liverpool. The Argentinian also presided over two unsuccessful Premier League title challenges and although Tottenham were never top during the 2015-16 and 2016-17 seasons, it added to the sense a growing trophy drought would never end.

Jose Mourinho

Serial-winner Mourinho was hired with a clear brief to help Spurs make the crucial last step and did take them to the Carabao Cup final, but failed to manage at Wembley after being dismissed following a run of three defeats in six matches, including a shock Europa League quarter-final exit to Dinamo Zagreb. Instead, rookie coach Ryan Mason went toe-to-toe with Pep Guardiola and unsurprisingly Tottenham lost 1-0 to Manchester City to make it four consecutive final defeats.

Antonio Conte

After Nuno Espirito Santo lasted only 17 matches, Conte was the next win-now manager Spurs chairman Daniel Levy turned to in a bid to end a frustrating trophy drought. Whilst Conte did take the club back into the Champions League, a one-sided two-legged Carabao Cup semi-final loss to Chelsea was followed by disappointing domestic cup losses to Nottingham Forest and Sheffield United before AC Milan eased past Tottenham in the last 16 of the Champions League. It made Conte the latest to try and fail to win at the north London club until Postecoglou pulled it off with a 1-0 win at San Mames on Wednesday night.