Despite plenty of positives at the north London club, including a new stadium, the hiring of Jose Mourinho and big-money signings such as Tanguy Ndombele, success in terms of titles has not been forthcoming.
Cottee, who played for the likes of West Ham and Everton, feels that Kane will chase silverware if Tottenham continue to fall short.
“I think there will come a time when he says ‘I’ve done as much as I can, I’ve scored lots of goals for Spurs but for many, many reasons it’s not happened’,” Cottee said on Sky Sports News.
“Everything is in place there. They’ve got a great stadium, great club, great fans etc. but they haven’t won anything.
“That’s what Harry will want to taste before he finishes his career. You want that feeling of winning the Premier League or Champions League and at the moment I can’t see him doing that at Spurs.
“I think it’s inevitable, if it doesn’t happen in the next year or so, I think Harry will leave – probably next summer.”
While Kane may look to move on, it would take an extraordinary fee to prise him away from Spurs, due to his long-term contract with the club.
Cottee feels that a world record level of transfer fee would be money well spent on Kane, though, as his goal record offers a guaranteed return.
“We saw [Kylian] Mbappe and Neymar go for huge amounts of money. Is Harry Kane worth that? Yes he is, he’s a goalscorer.
“If Harry was to go [to Old Trafford] you would expect him to score the goals to take Manchester United to the next level.
“For them, that is to try and regain that Premier League crown and to try and be more dominant in Europe again. I think Harry could do that for them.
“In the current market, if other players are worth what they paid for them, then Harry Kane, for me, is worth £200m all day long.”
Recent reports have suggested that Tottenham are keen to keep hold of their striker, however, while transfers for this coming summer are an uncertainty with regards to timing, as well as expenditure which clubs are willing to make.
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