Teddy Sheringham says Harry Kane will be a “very disappointed man” if he ends his career without winning a trophy.
The Tottenham and England talisman is third in the all-time Premier League goalscorers list with 203 strikes but the 29-year-old’s mantlepiece remains bare.
Kane’s wait to lift silverware will continue into next season at the earliest after Spurs were knocked out of both the FA Cup and Champions League in quick succession earlier this month.
Having made no secret of his desire to compete for football’s biggest prizes, Sheringham suggested there will be a tinge of regret if Kane does not get the trophy he deserves.
At the London Football Awards, the 56-year-old exclusively told LiveScore: “Football is all about winning stuff.
“If he goes throughout his career without winning stuff he’ll be a very disappointed man, with the player that he is.
“It’s all well and good getting these accolades you get for personal reasons but he’s in a team game and he needs to win things as a team.”
As has often been the case in recent years, Kane’s future in North London is poised to be under the spotlight as he enters the final year of his contract this summer.
Manchester United, who are a place above Spurs in third, have been strongly linked with the Lillywhites No10 after recently ending their own six-year trophy drought with victory in the Carabao Cup.
Sheringham, who won three Premier League titles after leaving White Hart Lane for Old Trafford in 1997, admits he is unsure where Kane sees his immediate future.
He added: “I really don’t know. I’ve probably had this conversation for the last three or four years about what Harry should do.
“He’s at a club that he loves but he wants to win things as well, so you’ll have to ask Harry.
“I keep getting in trouble every time I say what he should do!”
With Alan Shearer’s Premier League record in sight, Kane also became Tottenham’s all-time top goalscorer in February with his 267th goal in all competitions for his boyhood club against Manchester City.
He has since taken his tally to 270 with three more strikes — including two in a 3-1 win over Nottingham Forest on Sunday.
Fellow club legend Gary Mabbutt was keen to stress how fondly the striker holds Spurs in his heart.
The former defender said: “Harry came out at the end of the game the other day. We beat Forest, we had a fantastic result against Forest.
“Harry was questioned after that. He loves being at Spurs. I’ve known him since he was a young lad, his family are all based around here, he loves London.
“So that’ll be down to Harry’s choice in the end. I see no reason he should leave a club like Spurs.”