It is February 2008, a different time. Gordon Brown is Prime Minister. Heathrow’s Terminal 5 opens amidst chaos and confusion.

The Welsh singer Duffy is at number one in the charts asking for mercy while in the Premier League a fresh-faced, heavily-gelled Ronaldo is scoring a ridiculous amount of goals for Manchester United.  

The Reds would go on to win both the league and the Champions League that year while at the other end of the spectrum the football odds didn’t hold out much hope for Derby County, the Rams enduring a record-breaking, abysmal campaign. 

But we’re getting ahead of ourselves. It is February 2008 and Tottenham are in their first final for six years, facing Chelsea with a Carling Cup up for grabs.

They had lost last time out, also in the League Cup, undone by Blackburn and Andy Cole. Indeed, Spurs had yet to win a trophy in the 21st century, too often coming unstuck in quarter finals of the domestic competitions.

In the league meanwhile they were habitually mid-table fare, occasionally finding some consistency and breaking into the top six but all told, this was hardly a vintage period for the North London giants with several seasons to forget.

Nor was this a vintage team, that had navigated a path past Manchester City and arch-neighbours Arsenal to reach this showpiece event, held on an untypically mild afternoon. 

Up front there was Robbie Keane and Dimitar Berbatov, and with Jermain Defoe coming off the bench that’s one hell of an attacking roster. At the back, Woodgate and Kaboul were solid enough, and the brilliant Ledley King played when fitness allowed. 

It was their midfield that let them down, a coterie of ‘Spursy’ types who could perform wonders on their day but more times than not flattered to deceive. There was Jenas and Malbranque. Huddlestone holding.

This infuriating collection of unfulfilled potential had started 2007/08 in woeful fashion, winning only one of their opening 12 games but with Martin Jol gone in October, and Juande Ramos replacing him to install some order, improvements came. 

Points started to be picked up at home and running concurrent to this was their cup run that eventually led to two ferociously competed North London Derbies in the semis. With the Gunners dispensed with, a rare trip to Wembley beckoned.

Still, the online betting almost exclusively backed Chelsea to prevail, the Blues unquestionably the better team and just a few months away from a Champions League final encounter with United.

Chelsea had not finished outside of the top two in the Premier League for five years running. 

It didn’t surprise therefore when the favourites took the lead, Didier Drogba scoring in his usual clinical manner but to Spurs’ credit they stayed in the game, fashioning chances and troubling the always superb Petr Cech in nets. 

In the second period, they got their rewards for their perseverance with a penalty, one that in truth was six of one, half a dozen of the other, but Berbatov took full advantage all the same, tucking it away nicely.

And that’s how it remained until early into extra-time, when Jonathan Woodgate rose to bundle a winner home from close range. Half of North London celebrated wildly that evening. 

Such was Tottenham’s limitations at the time that nobody expected this victory to act as a springboard to greater success, and nor did it play out that way. Yet it remains a surprise that this was Spurs’ last trophy win, 15 years ago and counting.

Over to you Ange...


*Credit for all of the photos in this article belongs to Alamy*

Stephen Tudor is a freelance football writer and sports enthusiast who only knows slightly less about the beautiful game than you do.

A contributor to FourFourTwo and Forbes, he is a Manchester City fan who was taken to Maine Road as a child because his grandad predicted they would one day be good.