Harry Kane: The 27 former Tottenham players that left and won trophies elsewhere since 2008

Harry Kane set the wheels in motion for his Tottenham departure on Monday by telling the club that he wants to leave in the summer.

The 27-year-old has been left disappointed by his last few years at the club after coming so agonisingly close to finally ending Spurs’ trophy drought but, ultimately, always coming up short.  

Kane has two runners-up medals in the League Cup and one in both the Premier League and Champions League with Spurs and is yet to win a any sort of major trophy in his career.

Now with the time ticking on his career as a professional footballer, Kane feels that the only way he will break his trophy duck is by doing it elsewhere.

And judging by the evidence of those before him, laid out in analysis seen on Twitter, it wouldn’t be a bad idea.

Since Tottenham’s Carling Cup triumph in 2008, 27 players have left the club and have gone on to win silverware at other clubs. Spurs icon Jermain Defoe was one of the most recent to do so, getting his hands on the Scottish Premiership title under Steven Gerrard’s stewardship at Rangers.

But who are the other 26 former Spurs stars that abandoned ship to check if the grass was actually greener? Here Sportsmail takes a look at those players and what they won after leaving White Hart Lane. 

Dimitar Berbatov

Titles won: Premier League (x3) Club World Cup, English League Cup

One of the members of Spurs’ Carling Cup triumph, Dimitar Berbatov left that very summer and was granted a big-money move to Manchester United. The move paid off for the Bulgarian where he won three Premier League titles, a Club World Cup and a League Cup all during a four-year stint at Old Trafford.

Robbie Keane

Titles won: MLS Cup (x3), MLS Supporter’s Shield

Along with Berbatov, Robbie Keane was a part of the Spurs squad that beat Chelsea in the 2008 Carling Cup final at Wembley, where he would cement himself as a club legend. After a failed stint at Liverpool and then return to Spurs, Keane went on to LA Galaxy where he won four more titles, lifting the MLS Cup three times along with the MLS Supporter’s Shield.

Teemu Tainio

Titles won: Eredivisie, Finnish League (x2), Finnish Cup 

Another member of the Carling Cup squad, Teemu Tainio enjoyed more success across the continent, winning the Eredivisie with Ajax before winning the Finnish Cup and Finnish top flight on two separate occasions with HJK. 

Lee Young-pyo

Titles won: Saudi Arabian League (x2), Saudi Cup (x2)

Lee Young-pyo helped Spurs secure Carling Cup glory before leaving in the summer to join Borussia Dortmund for a year. While he won no silverware in Germany, the South Korean would finally get his hands on another trophy after moving to the Middle East, where he was the Saudi Arabian League and Saudi Cup on two different occasions with Al-Hilal.

Kevin-Prince Boateng

Titles won: LaLiga, Serie A, Italian Cup, German Cup

While Kevin-Prince Boateng’s time at Tottenham was brief and not at all noteworthy, he did play a part in helping the club reach the Carling Cup final but didn’t play in it. However, his time did eventually fizzle out and he was sold to Portsmouth. Boateng eventually made his way to AC Milan, where he won the Serie A and Supercoppa Italiana before winning more silverware in Germany and Spain.

Hossam Ghaly

Titles won: Egyptian League (x4), Egyptian Cup, CAF Champions League, CAF Confederation Cup

Another alumni of Spurs’ Carling Cup-winning squad, Hossam Ghaly eventually made his way back to his native Egypt where he enjoyed a lot of success. Ghaly went on to win the Egyptian League four times, the Egyptian Cup along with the CAF Champions League and CAF Confederation Cup with El Ahly Cairo.

Adel Taarabt

Titles won: Portuguese League, Portuguese Super Cup

Moroccan magician Adel Taarabt arrived at Spurs with plenty of potential but the north London club failed to harness it before he was allowed to leave 2009. While he did help QPR win the Championship and gain promotion back to the Premier League, Taarabt got his hands on some silverware when he won Liga NOS with Benfica in 2019. He also won the Portuguese Super Cup in that same year.

Tomas Pekhart

Titles won: Czech League, Polish League (x2), Israeli League, Greek Cup

Having featured for Spurs’ Under 18 side, Tomas Pekhart made his break away from White Hart Lane across Europe, winning the Czech League title, Israeli League title and the Greek Cup with AEK Athens.

Didier Zokora

Titles won: Spanish Cup

After tasting Carling Cup glory with Spurs in 2008, Didier Zokora came close to winning the trophy again the following season but fell short in the final against Manchester United. Zokora would only lift one more trophy after leaving Spurs where he would win the Copa del Rey with Sevilla in 2010.

Kyle Walker

Titles won: Premier League (x3), FA Cup, League Cup (x4), Community Shield (x2)

Having come close to winning breaking Spurs’ trophy drought in 2015 after finishing as runners-up once again in the League Cup, Kyle Walker departed Spurs for Man City in a record £54m move. Walker saw success straight away, winning the Premier League and League Cup double in his first year at the Etihad before going on to lift the FA Cup the following season. Walker would go on to collect two more Premier League winner’s medals along with three more Carabao Cups and two Community Shields.

Paul-Jose Mpoku

Titles won: Belgian Cup

Paul-Jose Mpoku arrived at Spurs’ youth academy in 2008 but left the club three years later without making a single senior appearance. He would try his hand at Italian and Greek football before returning to Standard Liege, where he had previously featured in their academy. He went on to lift the Belgian Cup in 2018 but that remained his only piece of silverware in his career.

Bongani Khumalo

Titles won: South African League (x4), South African Cup

Another strange purchase by Spurs that went on to achieve nothing at the club, Bongani Khumalo left the club without a trace, making just seven appearances for the Under 23s side before returning to Africa to play for SuperSport United. He went on to win the South African League four times while adding a South African Cup to his collection.

Roman Pavlyuchenko

Titles won: Russian Cup 

Roman Pavlyuchenko was signed by Tottenham off the back of an impressive showing at Euro 2008, where he was named in the Team of the Tournament. After a four-year stint in north London, Pavlyuchenko would go on to win the Russian Cup with Lokomotiv Moscow in 2015, which is the only title he has won since leaving Spurs.

Vedran Corluka

Titles won: Russian League, Russian Cup (x4), Russian Super Cup

Vedran Corluka, affectionately known as ‘Charlie’ in the Tottenham terraces, left the club after four years at the club in 2012 and would go on to finish his playing career out in Russia. It was there where he enjoyed the most success of his career, winning the Russian Premier League, the Russian Cup (four times) and the Russian Super Cup.

Simon Dawkins

Titles won: MLS Supporter’s Shield

Having rise through the ranks at Spurs, Simon Dawkins failed to break into the first team under Martin Jol. After leaving the club before returning for another three-year stint in 2011, Dawkins tried his luck across the pond with the San Jose Earthquakes. He would go on to win the MLS Supporter’s Shield during his time in North America. 

Luka Modric

Titles won: UEFA Champions League (x4), LaLiga (x2), Spanish Cup, Spanish Super Cup (x3), FIFA Club World Cup (x4), UEFA Super Cup (x3)

Arguably the former Spurs players that’s enjoyed the most success since leaving the club, Luka Modric went on to become an all-time great at Real Madrid, winning four Champions Leagues, two LaLiga titles, the FIFA Club World Cup four times and three UEFA Super Cups. While most other players on this list have won domestic cups in lesser-known leagues, Kane will be aiming to replicate what Modric has achieved should he leave Tottenham.

Rafael van der Vaart

Titles won: Danish League

A real fan favourite at the Lane, Rafael van der Vaart endeared himself to the club’s supporters when he arrived on deadline day from Real Madrid and his goals against Arsenal only made that much more popular. While he admits he left prematurely in 2012, he did get his hands on a trophy down the line, winning the Danish League with FC Midtjylland in the 2017-18 season. 

Gareth Bale

Titles won: UEFA Champions League (x4), LaLiga (x2), Spanish Cup, Spanish Super Cup (x2), FIFA Club World Cup (x4), UEFA Super Cup (x3)

Copy and paste from Modric. Arriving a season later than the Croatian, Bale has done it and won it all with Los Blancos. The Welshman is the most decorated British players to go overseas and is the man for the big occasion, scoring multiple times in Champions League finals. Another benchmark for Kane.

Jermain Defoe

Titles won: Scottish Premiership

Jermain Defoe became one of the most recent former Spurs players to win a trophy after leaving the club, as he helped Steven Gerrard’s Rangers side win their first Scottish Premiership title in over a decade – and they managed to do it while going undefeated.

Clint Dempsey

Titles won: MLS Cup, MLS Supporter’s Shield, US Open Cup

Former Fulham forward and part-time rapper Clint Dempsey left Spurs after just one season in 2013 and returned to the United States to see out the rest of his career with Seattle Sounders. He would lift the MLS Cup, MLS Supporter’s Shield and US Open Cup during his five years at the club before retiring.

Tomislav Gomelt

Titles won: Romanian Cup

Another player for the ‘didn’t play for Tottenham’ category, Tomislav Gomelt rose through the academy before being shipped out on loan a number of times without making a senior appearance. He would eventually find himself at Bari, but it was while he was out on loan at CFR Cluj that he would win the 2015-16 Romanian Cup.

Paulinho

Titles won: LaLiga, Spanish Cup, Chinese League (x4), Chinese Cup, Chinese Super Cup (x2), AFC Champions League

One of the seven players brought to the club using the ‘Bale money’, Paulinho was a complete flop at the club and would only last two seasons before Spurs cut their losses and sold him to China’s Guangzhou Evergrande in 2015. After winning back-to-back Chinese Super League titles, Paulinho was bizarrely bought by Barcelona but it proved to be a huge hit, with the midfielder helping the Catalan side win LaLiga and Copa del Rey in 2017-18 before returning to China.

Benjamin Stambouli

Titles won: Ligue 1, French Cup, French League Cup, French Super Cup (x2)

Benjamin Stambouli arrived at Tottenham in 2014 but didn’t stick around for long, and was promptly sold to PSG the following summer. He would complete the domestic treble in France before leaving for Schalke a year after that.

Vincent Janssen

Titles won: Mexican League, Mexican Cup

After striker that just didn’t cut it at the club was Vincent Janssen. Bought for £17m in 2016, the Dutchman was shown the exit three years later, where he would end up at Mexican outfit Monterrey. In his debut season for the club, Janssen managed to win the Mexican League and Mexican Cup to add his first bits of silverware to his CV.

Georges-Kevin N’Koudou

Titles won: Turkish League, Turkish Cup

Along with Defoe, Georges-Kevin N’Koudou is another former Spurs that has experienced title glory recently, with the Frenchman winning the Super Lig and Turkish Cup this season.

Christian Eriksen

Titles won: Serie A

While Kane is struggling for silverware in north London, former team-mate Christian Eriksen has managed to win the Serie A title with Inter Milan in his first full season at the club. The Dane has played a part in Antonio Conte’s Scudetto-winning squad that has stopped Juventus from winning 10 successive league titles.

Fernando Llorente

Titles won: Italian Cup

Fernando Llorente played second fiddle to Kane during his stint at Spurs and was allowed to leave after the club’s Champions League final defeat in Madrid. In his first season with Napoli, the Spaniard won the Coppa Italia, beating Juventus in the final.