Jonathan Woodgate says Tottenham must start delivering trophies to keep hold of Harry Kane but is not convinced lifting the Carabao Cup will be sufficient.
Former defender Woodgate cemented his place in Spurs folklore by securing the club's last piece of silverware courtesy of an extra-time winner against Chelsea in the 2008 League Cup final.
Tottenham will seek further Wembley glory in that competition on Sunday when they take on holders Manchester City.
Striker Kane, who is doubtful for the game due to an ankle injury, is yet to win a major honour and Woodgate believes the north Londoners need to end the 13-year trophy drought and commit to additional investment to prevent their star man eyeing a move elsewhere.
"They have to [start winning silverware] with the stadium they have built and with the players they have got," said Woodgate, who manages Championship side Bournemouth.
"They have got the best striker in England in Harry Kane so they need to start winning trophies for him. They're a well-run football club but they need to start soon."
Asked if breaking City's three-year stranglehold on the cup would be enough to appease Kane, Woodgate replied: "I am not sure.
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"They will need more investment for Harry Kane to stay, I'm sure of that.
"He's been unbelievable again this season and scored so many goals and even evolved as a player by making so many assists.
"He's an incredible talent so I would say Spurs need to invest to keep Harry Kane at the club."
Woodgate was making only his fifth Tottenham appearance when he unconventionally capitalised on an error by Chelsea goalkeeper Petr Cech to snatch the 2-1 win in 2008 after a Dimitar Berbatov penalty cancelled out Didier Drogba's free-kick opener.
Despite finishing runners-up in the Premier League and Champions League under Mauricio Pochettino in recent years, the club have not added to their trophy cabinet since.
Spurs look likely to miss out on Champions League qualification for a second successive season and will run out at the national stadium at the end of tumultuous week which included a failed attempt to join an elite European Super League and the sacking of Jose Mourinho.
Rookie manager Ryan Mason is tasked with halting the prolonged barren spell after being thrust into the Tottenham hot seat at the age of just 29 following Mourinho's departure.
Woodgate was in the Tottenham side when Mason - who was forced to retire in 2018 because of a fractured skull suffered playing for Hull - made his professional debut in a UEFA Cup win over Dutch club NEC Nijmegen in 2008.
The 41-year-old is familiar with unexpected managerial opportunities having succeeded the sacked Jason Tindall in February just two days after joining Bournemouth as a coach and has urged Mason to make the most of his "live interview".
"He must be well thought of at the football club to be given the reins until the end of the season. It's fair play to Ryan," said Woodgate.
"He was unfortunate to finish his career early through a horrendous injury but now he's in coaching, he's got an incredible opportunity.
"I'm absolutely over the moon for him and he's Spurs through and through so he's someone the fans can relate to.
"It's like a live interview. You never know what's going to happen.
"They've come close under Pochettino, who is a fantastic manager, Mourinho got them to the final but now it's up to Ryan."
Former England international Woodgate, who also represented Leeds, Newcastle, Real Madrid, Middlesbrough and Stoke in his playing days, was named man of the match for his influential cup final display against Chelsea after being selected to start following an injury to Michael Dawson.
Winning at Wembley under the management of Spanish coach Juande Ramos was a career highlight for the retired centre-back and remains a constant talking point when he bumps into Tottenham fans.
"It's the only trophy I won so it's got to be one of my best moments as a player," he said.
"It's part of the club's history now of being there and winning that last trophy for them. I am sure sooner or later they are going to win a trophy.
"But to give the Spurs fans that day - especially beating Chelsea - was something special for them and really something special for me.
"I still speak with some of the players now from that era and they are great memories.
"And every time I see a Spurs fan, that's all they ever say to me: 'I was there when you scored'. It was a great day."
Woodgate's winner's medal and man-of-the-match trophy are currently housed in his son's bedroom, while his match-worn shirt is tucked away in a wardrobe.
Tottenham, who finished 11th that season, came crashing back down to earth a week later, losing 4-1 at soon to be relegated Birmingham.
Woodgate sat out at St Andrew's due to an ankle issue and struggled to contain a smile when asked if the post-final party contributed to the subsequent heavy defeat.
"The celebrations were really good, to be honest with you. You've got to enjoy those moments because they don't happen all of the time," he said.
"I definitely enjoyed it - I think all of the other players did.
"It was huge for us because not many of us had won a trophy at that time and to beat a Chelsea team firing on all cylinders was good.
"We weren't consistent enough in the league but in cup competitions we could beat anyone."
Manchester City and Tottenham look to get their hands on silverware when they do battle at Wembley in Sunday's Carabao Cup final.
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