Tottenham legend Teddy Sheringham: 'The worst thing Harry Kane could do would be to sign a new contract at Spurs'

Tottenham striker Harry Kane applauds the fans after his side's 2-2 draw at home to Manchester United in April 2023.
(Image credit: Getty Images)

Tottenham all-time scorer Harry Kane should resist any efforts to get him to sign a new deal ahead of the new season. 

That is the advice on offer from Tottenham Hotspur legend Teddy Sheringham, who believes the England captain needs to keep his options open even if he isn't sold before the transfer window shuts. 

“I think the worst thing that Harry Kane could do would be to sign a new contract this summer," Sheringham tells Lord Ping. "He could be in a situation where things don’t go to plan with Ange and then he’s in a cycle where he has to wait for a new manager to come in. 

"If he goes into the season without a new deal, he can watch how everything unfolds. Harry Kane will still be completely focussed on scoring goals for Tottenham and doing his best for the club. The dream scenario would be for him to perform well next season and be convinced that his future remains at the club.”

Sheringham also feels Kane is in a similar position to him when he made the decision to leave Spurs for Manchester United in 1997. Sheringham would go on to play a crucial role in a glittering spell for the Red Devils, scoring crucial goals as Sir Alex Ferguson's side clinched a treble in 1999. 

“Harry is in a very similar situation to where I was with the club," the former England man explains. "He will want the best players playing alongside him and he will want to be playing against the best players in the Champions League, obviously that isn’t happening at Tottenham this season. I really hope that he stays, but I don’t expect him to make the decision anytime soon.”

More Tottenham stories

Alan Shearer has joked that he'll "drive Kane's f****** car there [Bayern Munich] myself" in order to protect his Premier League goalscoring record.

Meanwhile, former striker Teddy Sheringham reckons that, "No Tottenham fan would begrudge him the opportunity to win trophies with another club".

Tottenham transfer news is also ramping up, with Ange Postecoglou now confirmed as manager. Roger Ibanez has been linked, as has Liverpool no.2 Caoimhin Kelleher and long-time target Paolo Dybala.

Ed McCambridge
Staff Writer

Ed is a staff writer at FourFourTwo, working across the magazine and website. A German speaker, he’s been working as a football reporter in Berlin since 2015, predominantly covering the Bundesliga and Germany's national team. Favourite FFT features include an exclusive interview with Jude Bellingham following the youngster’s move to Borussia Dortmund in 2020, a history of the Berlin Derby since the fall of the Wall and a celebration of Kevin Keegan’s playing career.

Read more
MUNICH, GERMANY - FEBRUARY 01: Harry Kane of Bayern Munich celebrates scoring his team's third goal during the Bundesliga match between FC Bayern München and Holstein Kiel at Allianz Arena on February 01, 2025 in Munich, Germany. (Photo by Alexander Hassenstein/Getty Images)
'I can see the logic with Harry Kane joining Arsenal - he would be the perfect last piece in the jigsaw and suits them down to the ground': England captain touted for shock transfer to Tottenham's rivals
MUNICH, GERMANY - FEBRUARY 01: Harry Kane of Bayern Munich celebrates scoring his team's third goal during the Bundesliga match between FC Bayern München and Holstein Kiel at Allianz Arena on February 01, 2025 in Munich, Germany. (Photo by Alexander Hassenstein/Getty Images)
Harry Kane could return to Premier League for a lot less than you think, with Bayern Munich release clause revealed: report
Daniel Levy
‘It’s not Daniel Levy’s fault that Spurs haven’t won a trophy – they can win one under him, and I think they can still win one this season’ Former Tottenham Hotspur boss offers his backing to under-fire chairman
BIRMINGHAM, ENGLAND - FEBRUARY 09: Ange Postecoglou manager / head coach of Tottenham Hotspur after the Emirates FA Cup Fourth Round match between Aston Villa and Tottenham Hotspur at Villa Park on February 09, 2025 in Birmingham, England. (Photo by Catherine Ivill - AMA/Getty Images)
Tottenham looking to sign player who has an Arsenal tattoo: report
BIRMINGHAM, ENGLAND - FEBRUARY 09: Ange Postecoglou manager / head coach of Tottenham Hotspur after the Emirates FA Cup Fourth Round match between Aston Villa and Tottenham Hotspur at Villa Park on February 09, 2025 in Birmingham, England. (Photo by Catherine Ivill - AMA/Getty Images)
‘I still back Ange Postecoglou – people haven’t respected what he’s said, that injuries have made a massive difference’ Tottenham Hotspur legend defends manager from criticism
MUNICH, GERMANY - MARCH 08: Harry Kane of Bayern Munich reacts during the Bundesliga match between FC Bayern München and VfL Bochum 1848 at the Allianz Arena on March 08, 2025 in Munich, Germany. FC Bayern will wear a special anniversary collection kit to mark the club’s 125th anniversary. (Photo by Alexander Hassenstein/Getty Images) Liverpool striker
Liverpool 'at the front of the line' to bring Harry Kane back to the Premier League: report
Latest in Interviews
Stuart Pearce Non-League Day
'It’s absolutely essential that funding drips down from the top end of the game' Stuart Pearce takes the Premier League trophy back to his non-league roots
Aston Villa manager Unai Emery looks on from the dugout during the Champions League last 16 first leg match against Club Brugge at Jan Breydel Stadium in Bruges, Belgium on 4 March, 2025
'Aston Villa have been fantastic in the Champions League and had some big victories against big sides. They can compete against PSG' Former Villain on why Unai Emery's side could spring a European shock
RB Leipzig star Benjamin Henrichs in action against Bayern Munich
'When you’re in the stadium, there are 70,000 people and they’re screaming - to hear your own leg pop was a real shock' RB Leipzig star Benjamin Henrichs on the Achilles rupture that changed his life - and how rehab abroad helped
Thomas Tuchel smiles after being announced as England head coach, October 2024
‘The fact he’s on a short deal doesn’t sit well. Gareth laid the foundations for players coming through. All Tuchel’s got to worry about is the here and now’: England hero lays out his issues with Thomas Tuchel appointment
‘In terms of credentials, he’s fantastic, but it’s our country against yours – if Southgate won the World Cup with Germany, what would English people say?’: Ex-Englaand striker weighs in on Thomas Tuchel and the foreign manager debate
Thomas Tuchel has been appointed the new England manager
‘England supporters are craving some success. If Tuchel can come in and finish the brilliant job Gareth Southgate started, nobody will care if he leaves’: Ex-Three Lions international gives his take on Thomas Tuchel's short-term deal
Latest in News
Fulham manager Marco Silva looks on from the dugout ahead of the FA Cup fourth round tie against Wigan Athletic at the Brick Community Stadium in Wigan, England on 8 February, 2025
'I think Marco Silva is the best manager in London - he managed to really maintain the desire to play attractive football, which was really hard over the years': Former Fulham talisman showers praise on 'impressive' Marco Silva
Manchester United head coach Ruben Amorim looks on following his side's defeat against AFC Bournemouth
Report reveals 10 Manchester United players leaving this summer
James Maddison of Tottenham Hotspur scores their 2nd goal during the Premier League match between Manchester City FC and Tottenham Hotspur FC at Etihad Stadium on November 23, 2024 in Manchester, England.
Tottenham and Manchester City could smash transfer record for British wonderkid: report
Tottenham Hotspur back row (L-R) Dele Alli, Mousa Dembele, Eric Dier, Davinson Sanchez, Hugo Lloris, Jan Vertonghen; front row (L-R) Son Heung-min, Christian Eriksen, Harry Kane, Kieran Trippier, Ben Davies during the Champions League match against Juventus at the Wembley Stadium on March 7, 2018 in London United Kingdom
Tottenham cult hero calls retirement - to avoid 'painkiller dependency'
Thomas Tuchel will take charge of England for the very first time this evening
'He pushed us. It was tough love, but that's Thomas' Former player reveals that the new England manager will be HARD on his players
Arsenal squad for 2024/25 LONDON, ENGLAND - AUGUST 11: William Saliba of Arsenal celebrates scoring his teams first goal with teammates during the Pre-Season Friendly match between Arsenal FC and Olympique Lyonnais at Emirates Stadium on August 11, 2024 in London, England. (Photo by David Price/Arsenal FC via Getty Images)
Arsenal warned, as Real Madrid are coming for their star next: report