When was the last time Tottenham Hotspur won a trophy?; League Cup final 2007-08; Ange Postecoglou

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On February 24 2008, Fidel Castro retired as president of Cuba, No Country for Old Men was named best picture at the Academy Awards and Flo Rida's Low was topping the charts.

It was also the day Tottenham Hotspur won their last title.

That's right, it's been 17 years between celebrations for Spurs fans. It may be about to end, through the workings of an Aussie, Ange Postecoglou.

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As expected, not a single player from that 2008 League Cup final squad is at the club anymore.

The location of the Chelsea vs Tottenham fixture was the new Wembley Stadium.

Spurs were coming off a 6-2 aggregate win in their semi-final against arch rivals Arsenal. The second leg was a 5-1 win at home.

Just like this year, there was a drought to end too. Nine years in fact.

Tottenham's final side included big names like Jermaine Jenas, Robbie Keane and Dimitar Berbatov. On the other side of the spectrum, Chelsea had Petr Čech, John Terry, Wayne Bridge, Frank Lampard, Michael Essien, Nicholas Anelka and Didier Drogba.

Back then Spurs were falling behind expectations. In the 2002-03 Premier League season they finished 10th. 14th, 9th, 5th and 5th followed.

Earlier in the season, Martin Jol was sacked after a horrendous start to the season. Daniel Levy was the chairman at the time, and still is.

Jaunde Ramos arrived and said the team were 100kg overweight overall. Fitness coach Marcos Alvarez claimed in February the weight had halved. Sugar was limited for the players, eventually striker Darren Bent claimed that led to the team turning on the manager.

But it must have had some impact, with Spurs 90 minutes from a trophy.

Well that turned into more than 90 minutes.

Drogba took the lead for Chelsea in the 39th minute. His free kick sat well outside the box and was hit low into the bottom right corner. Spurs keeper Paul Robinson stood still as it went past.

At half time, the score sat at 1-0.

As always in a final, a spot of controversy arrived. Tom Huddlestone tried to control the ball in the box as Bridge approached. Huddlestone ran towards the touchline referee, protesting a handball. It was given, and rightly so.

Berbatov sent Čech the wrong way and it was 1-1. It stayed the same by full time.

Extra time arrived and three minutes in, Spurs had the lead.

Jenas delivered a free kick, and Čech left his goal-line to parry it. Instead, he punched the ball into Jonathan Woodgate's head and it was a goal.

Eventually the full time whistle blew and it was euphoria around Wembley. A dramatic comeback, fitting for a final.

"Who knows, it might signify a much bigger comeback for the club," was said on commentary.

Not quite.

Since then there's been many false dawns. Spurs lost the next League Cup final on penalties to Manchester United.

Once again in 2014-15, the League Cup was lost and this time it was Chelsea winning 2-0.

In the 2016-17 Premier League season, Harry Kane was the leading goalscorer with 29. Four better than Romelu Lukaku. But Spurs finished second to Chelsea, who won by seven points.

Then came one of the club's biggest matches ever, the 2018-19 Champions League final.

It was Mauricio Pochettino's crowning glory as Spurs coach. Liverpool ultimately won 2-0 and the drought continued.

In 2020-21, the League Cup losses mounted. Manchester City won 1-0 in the final this time. This match lives long in the memory of Spurs fans considering Jose Mourinho was sacked a week before the final.

But now it's Postecoglou's turn to rewrite the history books.

This year, English Football has been the year of the underdog.

In the League Cup, Newcastle ended a 56-year drought. Crystal Palace's FA Cup win over City was their first major trophy, ending a 120-year wait.

United are currently the slight favourites with the bookmakers for the Europa League final, putting the trend in Spurs' favour.

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