When was the last time Tottenham won a trophy?

Jose Mourinho might be at the helm of a new era at Tottenham, the Portuguese manager having earned a solid track record of regularly winning trophies at clubs.

"It has been a long time coming, we've been one of the best teams in the world in the years we've been together, we deserve a trophy," Dele Alli said in February.

"No-one is going to give it to us, we have to keep pushing – and not just for us, but for the fans – we have to win something."

But how long has it been since Tottenham last tasted silverware?

Tottenham's last trophy was the 2008 Carling Cup, when they beat Chelsea 2-1 in the final at Wembley.

It marked the fourth time that Tottenham were crowned League Cup winners.

Juande Ramos' Tottenham team beat crosstown rivals Arsenal 6-2 in the semi-final, earning them a clash against the Blues.

Chelsea were defending champions of the trophy, having beaten Arsenal in the 2007 final.

Didier Drogba scored a free-kick in the first half to give Chelsea the lead going into the break, but Dimitar Berbatov scored a penalty in the 70th minute after a Wayne Bridge penalty to even out the scoreline.

Jonathan Woodgate then netted three minutes into extra-time after converting a free-kick taken by Jermaine Jenas that clinched the victory.

It was Tottenham's first trophy in nine years, and it was an especially important one. With it, they secured UEFA Cup qualification for the next season – something that they had failed to do through their Premier League campaign as they finished 11th in the table.

The 2008 Carling Cup final was the first League Cup final to be played at the newly-built Wembley Stadium, with the previous finals held at Cardiff's Millennium Stadium.

Though Mauricio Pochettino's Tottenham side was lauded as one of the strongest Premier League sides in recent years, they failed to win any silverware during the Argentine's five years at the club.

Despite the goalscoring prowess of striker Harry Kane, who has won two Premier League Golden Boots, he has yet to lift a trophy with Tottenham.

The Lilywhites launched a Premier League title bid in 2015-16 and spent most of the season as frontrunners, but ultimately conceded the league to champions Leicester City.

The north Londoners came close to silverware again in 2019, when they reached the Champions League final in Madrid against Premier League rivals Liverpool, but ultimately lost 2-0.

They had mounted an incredible semi-final comeback against Ajax that saw them win the tie 3-3 on away goals after losing the first leg 1-0 at home, but came up short in the final.

Mohamed Salah's penalty for the Reds in the second minute, coupled with Divock Origi's 87th-minute goal, ensured that Tottenham would be forced to wait out their trophy drought for a little while longer.