Where are they now? The last Tottenham side to win a trophy | OneFootball

History awaits Tottenham Hotspur, who have the opportunity to end a 17-year trophy drought as they prepare to face Premier League rivals Manchester United in the 2025 Europa League final.

Head coach Ange Postecoglou has confidently stated that he typically wins silverware in his second year managing a club. The determined Australian manager could fulfil that promise in Bilbao.

This will not be the first time that Spurs have aimed to secure a trophy since their 2008 League Cup victory. Under former manager Mauricio Pochettino, they faced disappointment twice: losing to Chelsea in the 2016 League Cup final and to Liverpool in the 2019 Champions League final. The latter was an all-English final held in Spain.

Additionally, there was controversy surrounding the sacking of Jose Mourinho just days before the 2021 League Cup, which they subsequently lost to Manchester City.

But let’s take a moment to reflect on the members of that 2008 League Cup-winning side—the starting eleven and three substitutes who ran out 2-1 winners over Chelsea after extra time—and see where they are now.

GK: Paul Robinson

Having joined from his boyhood club, Leeds United, four years prior, Tottenham during this period could rely upon England’s number one between the sticks. Robinson, more often than not, was a reliable goalkeeper but conceded a 39th-minute opener to Didier Drogba, though he shut Chelsea out for the remainder of the game. This outing proved to be one of Robinson’s last in a Spurs jersey, as he left for Blackburn Rovers in the summer. There, the Yorkshireman enjoyed seven more professional seasons, four of those being in the Premier League. After departing Ewood Park, it was a short trip to Burnley where the 41-time-capped Three Lions international hung up his gloves.

RB: Alan Hutton

After making waves at Rangers, it was only a matter of time before Alan Hutton journeyed south, and it was Tottenham that secured his signature on 30 January 2008, less than a month before this final. If Hutton thought this would be the first of many appearances at White Hart Lane, he was sadly mistaken, as in the forthcoming three seasons, they would not get close to replicating that achievement.

The Scotsman’s playing minutes were limited due to niggling injuries, as well as being usurped by Croatian international Vedran Corluka (a favourite of Ramos’ successor, Harry Redknapp) on the right-hand side of the Spurs defence. Aston Villa would acquire Hutton before loaning him to Nottingham Forest, Mallorca, and Bolton Wanderers. It was at Villa Park where Hutton, a 50-time capped Scottish international, decided to call time on a near two-decade career.

CB: Jonathan Woodgate

If a word could sum up Jonathan Woodgate’s career, it would be unfulfilled. He played less than 400 matches in official competitions during a span of 18 years, but it should have been more if not for those pesky injuries.

Seen by many observers as English football’s next great centre-back when he broke through at Leeds United (which proved to be the only club where he amassed over 100 league appearances), Newcastle enjoyed him for a season before Real Madrid moved in for his services. They signed him while he was injured, meaning he missed the entirety of his first season following that move, and when he did eventually debut, Woodgate endured one of the more humiliating debuts (own goal and sending off). He played 13 more times for Los Blancos before rehabilitating at Middlesbrough, and that was enough for Tottenham to come calling.

Woodgate enjoyed four seasons in North London and became a club legend after netting a 94th-minute winner over Chelsea. However, he only made four appearances in all competitions during his last two seasons. A final Premier League season with Stoke City was followed by four more years in the Championship with Boro, and after his retirement, he briefly managed them.

CB: Ledley King

A one-club man, much like Woodgate if not for injuries, Ledley King would be in the conversation for the Premier League’s most outstanding central defender.

When available, he showcased plenty of evidence of his brilliance. However, toward the latter part of his career, King struggled with chronic knee problems for which no effective treatment was found. Instead of training with the rest of the squad, he conducted fitness exercises on his own, which enabled him to participate in one first-team game per week. His former manager, Harry Redknapp, described King as “an absolute freak” for his ability to perform at a Premier League level despite not training regularly.

King announced his retirement from all forms of football in July 2012 due to the chronic knee injuries that had plagued much of his career. In August 2020, he was appointed as the assistant first-team coach, working alongside Jose Mourinho and the other coaching staff at Tottenham. Following Mourinho’s sacking, King returned full-time to his role as a club ambassador.

LB: Pascal Chimbonda

A whirlwind debut Premier League season with Wigan caught the eye of many, enough for Tottenham to sign Pascal Chimbonda. He would spend two seasons in North London before embarking on an incredible journeyman career — which saw him briefly return in 2009 — with stops along the way, including Blackburn Rovers, Queens Park Rangers, Doncaster Rovers, Market Drayton Town (in Northern Premier League Division One South), Carlisle United, Arles-Avignon (in Ligue 2), Washington (in Northern Premier League Division One), and Ashton Town (in North West Counties Football League Division One North). He recently served as player-manager of English non-league club Skelmersdale United.

RM: Aaron Lennon

Picking up 21 caps for England seems too few given Aaron Lennon’s talents, but such was the calibre of players available to those managers, perhaps it was a fair return. For a period, he was one of the most formidable players in his position in Premier League football. Lennon, another who came through at Leeds, was a mainstay for Tottenham across nine seasons, making no fewer than 22 appearances in those campaigns.

He left for Everton on loan in his final year before making that move permanent. His first season at Goodison Park proved to be Lennon’s hurrah, with him more or less becoming a squad player before performing the same duty with Burnley. That was until Süper Lig outfit Kayserispor gave him a new lease of life, enabling him to make 28 appearances for Burnley in the 2021–22 Premier League season. He registered two goals, his most in a single campaign since his aforementioned temporary Everton stay in 2014–15.

CM: Jermaine Jenas

Another who made 21 international appearances due to stiff competition for a place in England’s central midfield. But Spurs could always count on Jermaine Jenas, who built a steady reputation at Nottingham Forest, where he turned professional, and Newcastle United, where he became an established member of England’s squad.

His leadership qualities saw him lead out Spurs on occasions, but as the club started to move in a new direction, Jenas returned to Forest on loan before departing for Queens Park Rangers, where injury finally forced his retirement. While still recuperating from his final injury, he moved into media work as a pundit, a role he continued beyond retirement, including for the BBC on Match of the Day.

CM: Didier Zokora

Tottenham proved to be Didier Zokora’s only experience of English football, joining the Lilywhites in the summer of 2006 following his performances for the Ivory Coast. A midfield slot was vacant following Michael Carrick’s move to Manchester United. The Abidjan-born defensive midfielder spent three seasons at White Hart Lane before departing for Sevilla, where he lifted the Copa del Rey. After leaving Spain, he had a spell at Trabzonspor, before brief stays at fellow Turkish side Akhisarspor, as well as Indian Super League outfits Pune City and NorthEast United. Zokora ended his career after representing the Indonesian side Semen Padang.

LM: Steed Malbranque

When a former British prime minister names you among his favourite footballers, that brings a different kind of attention, but Steed Malbranque never allowed Tony Blair’s praise to faze him. He continued to put in good work at Fulham, which caught Tottenham’s attention. He enjoyed two seasons in North London, culminating in League Cup success.

Sunderland would soon enjoy his services before a return home, first turning out for Saint-Étienne and then his boyhood club Lyon, where he made over 100 appearances before initially moving across the Channel. Caen, Chasselay MDA, and Limonest would have Malbranque on their books before the Frenchman called time on his career.

CF: Robbie Keane

This final took place in Robbie Keane’s first spell with Tottenham, and some months after lifting this prize, the Republic of Ireland’s all-time leading goalscorer departed for Liverpool, where he struggled to recapture the Spurs form that saw him strike 80 goals across 197 league appearances.

Even after returning, Keane would be loaned out to Celtic and West Ham before following in David Beckham’s footsteps by joining LA Galaxy, with Indian outfit ATK turning out to be his final stop in an incredible career that began at Wolves before Coventry City, Inter Milan, and Leeds signed him.

Once no longer a professional footballer, Keane moved into management with ATK as his first coaching job, and since then he has led Maccabi Tel Aviv and currently Ferencvaros.

CF: Dimitar Berbatov

Just when Chelsea seemed to have control of the 2008 League Cup final, the enigmatic Dimitar Berbatov produced the leveller, turning the final on its head and switching momentum back to Spurs.

This success proved to be one of the final games Berbatov would play in a Spurs jersey, with a forthcoming switch to Manchester United, where he lifted two Premier League titles as well as another League Cup.

After departing Old Trafford, the Bulgarian marksman represented Fulham, Monaco, and PAOK before saying goodbye to the professional game with Indian Super League outfit Kerala Blasters.

Substitues

Younes Kaboul

So much was promised regarding Younes Kaboul, who came through at Auxerre, but his initial spell with Tottenham lasted a season before joining Portsmouth and then returning. However, of the six campaigns of that second period with Spurs, he managed to make over 13 league appearances in only two, with injuries and competition for places in central defence limiting his appearances.

After departing for Sunderland, where he again spent one year, Kaboul enjoyed two more professional seasons with Watford, where again his body failed him. Following an exit by mutual consent, he expressed a desire to go into coaching, which has yet to bear fruit.

Teemu Tainio

Kaboul somewhat followed in Teemu Tainio’s footsteps, as the 64-time Finnish international had also joined Spurs from Auxerre. He enjoyed three seasons with the North London club before representing Sunderland and Birmingham City (albeit on loan) in the Premier League, plus two league matches for Ajax, as well as MLS outfit New York Red Bulls, which led to a return home with HJK.

After hanging up his boots, Tainio moved into coaching with Haka, the first professional team he represented, giving him that managerial opportunity. He most recently coached Tallinna Kalev, and there have been spells in which he served as an assistant coach, notably with the Finland national team.

Tom Huddlestone

Here was the Carrick successor many Tottenham fans hoped for, but Huddlestone never reached the heights of his former teammate. His four international caps with England spanned between 2009 and 2012, with none gained while he played for Hull City and boyhood club Derby County (from where he joined Spurs). He curiously signed for Manchester United to end his career but represented their U21 side, where he fulfilled a coaching role. Huddlestone is now the Birmingham City first-team assistant coach.

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