The 2008 League Cup final was the first to be played at the new Wembley and Tottenham’s first trophy in 9 years.
Despite having finished outside the top 10 only once in the last 12 seasons, Tottenham have not had a great deal of success in cup competitions in that time.
Somewhat ironically, their solitary cup win came in the season in which they did finish outside the top 10, the 2007/08 season under Juande Ramos.
Spurs had a difficult league campaign under the Spaniard, who didn’t last long in North London, but victories over Middlesbrough, Blackpool, Manchester City and Arsenal set up a final against Chelsea.
Chelsea’s Frank Lampard celebrates winning the 2007 Carling Cup
Chelsea were the defending champions, having beaten Arsenal in the League Cup final in 2007.
There was an air of inevitability about the first goal, coming from Didier Drogba, a man who thrived on the hallowed turf of Wembley and in cup finals in general.
Spurs fought back though, high on confidence following a 5-1 defeat of Arsenal in their semi-final second leg.
Dimitar Berbatov restored parity from the penalty spot on 70 minutes, sending the game to extra time, where Jonathan Woodgate scored Tottenham’s winner in the 94th minute.
Jonathan Woodgate scores Tottenham’s winner 4 minutes into extra time
Eight years on and Tottenham haven’t won a trophy since that League Cup success, with reaching the final of the same competition the following year the closest they’ve come.
We take a look at Tottenham’s 2008 League Cup final team and see where they are now:
Goalkeeper: Paul Robinson
Beverley-born shot stopper Paul Robinson was between the sticks when Tottenham won the League Cup, and had been England’s number one up until a year earlier.
Robinson had a shaky season for Spurs in 2007/08, and made another mistake in the final. He left the club that summer, replaced by Heurelho Gomes. Robinson is now backup to Tom Heaton at Burnley.
Right-Back: Alan Hutton
Alan Hutton now plays for Aston Villa
Tottenham’s right-back in the 2008 final was Scotland international Alan Hutton. The then 26-year-old full-back joined the club in January 2008 from Rangers, and a month later he’d won his first piece of silverware.
Hutton’s career has been up and down since then, having had loan moves to the likes of Bolton and Mallorca. The full-back is currently contracted to Aston Villa but finds himself behind Richie De Laet in the clubs pecking order.
Centre-Back: Jonathan Woodgate
Injury prone but a magnificent defender on his day, Woodgate joined Tottenham from Middlesbrough after a tough stint at Real Madrid.
The England international scored Tottenham’s winner in the final and stayed at the club until 2011.
He retired from playing the game this summer, aged 36, having won promotion with his boyhood club Middlesbrough. Woodgate has since found work as a scout for Liverpool, working in Spain and Portugal.
Centre-Back: Ledley King
Ledley King Guest XI’s Ledley King gestures to the fans after being substituted
Both of Spurs centre-backs for the 2008 League Cup final could be described as injury prone but absolute class acts.
Both Woodgate and King were capable of playing at the very highest level and would have done were it not for injuries hampering their careers.
A Tottenham legend, King spent his entire 13 year career at White Hart Lane, making 321 appearances. The 35-year-old now works as an ambassador for Spurs.
Left-Back: Pascal Chimbonda
France and Guadeloupe international Pascal Chimbonda spent 2 years as a regular at White Hart Lane, before making a brief return in 2009.
The left-back became something of a nomad later in his career, and even found himself playing non league football in Shropshire in 2013.
The 37-year-old is currently a free agent, and has been for more than 18 months, having left French side AC Arles-Avignon in early 2015.
Right-Wing: Aaron Lennon
Aaron Lennon now plays for Everton
A long servant to Tottenham, having spent a decade with the North Londoners, Aaron Lennon was sold to Everton by Mauricio Pochettino last season.
The pacy and diminutive wide man played 364 games for Spurs, more than that of club legend Ledley King.
Central Midfield: Jermaine Jenas
Another player from this Spurs XI to have struggled with injuries towards the tail end of their career, Jermaine Jenas retired early, at the age of 31.
He spent 8 years in Tottenham’s midfield, before spending a season at QPR, where he eventually hung up his boots in 2014. Jenas now works as a pundit.
Central Midfield: Didier Zokora
Ivorian holding midfielder Didier Zokora hasn’t scored a goal in 12 years of professional football, which is an indication of the type of work Zokora does for the team.
A first team regular at Tottenham for three seasons before heading to Sevilla, Zokora is now 35, and recently joined Indian Super League outfit North East United.
Left Wing: Steed Malbranque
Steed Malbranque playing for Sunderland against York in 2013
Belgian-born midfielder Steed Malbranque was an often underrated player. Having started his professional career with Lyon, he joined Spurs after 5 years at Fulham.
Malbranque spent two seasons in North London before moving on to Sunderland. After 4 years back at Lyon, the 36-year-old joined Ligue 1 side Caen this summer.
Centre-Forward: Robbie Keane
Robbie Keane’s career since leaving Tottenham has been very well-profiled. The Irishman recently retired from international football having scored 68 goals for his country.
Keane spent 8 years with Spurs, in two separate spells, before leaving for LA Galaxy. Now in his fifth season for the Galaxy, Keane is the 15th highest scorer in MLS history.
Centre-Forward: Dimitar Berbatov
Dimitar Berbatov most recently played for PAOK
Quite simply a class act, Dimitar Berbatov is one of many people’s favourite ever Premier League players.
Cool, calm and nonchalant, supporters could even forgive the Bulgarian for not breaking a sweat, such was his quality on the football pitch.
A goal scorer for Tottenham from the spot in the final, he left the club that year to join Manchester United. Eight years on and the striker is a free agent, who spent last season playing in Greece.
How would you rate Tottenham’s 2008 League Cup final starting XI?
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