The England international has seen his future called into question on a regular basis since establishing himself as one of the most prolific strikers in world football.
Any number of clubs would welcome the opportunity to add him to their ranks, but a home-grown talent has remained loyal to Spurs and committed to a long-term contract last summer.
He is expected to continue honouring that agreement, although former Tottenham star Waddle concedes that his ambition will need to be matched in order for future interest to be fended off.
“Harry Kane won't leave Tottenham this summer, but his head will eventually turn towards winning trophies,” Waddle told Sportingbet.
“Real Madrid can practically guarantee that, as well as a very generous pay rise. He seems very settled at Tottenham and he's enjoying his football, but when he looks back at his career he will want his goals to have secured medals.
“Kane will look at the future of Tottenham once they move into the new stadium and he'll decide on his future from there. He can get in to any team in the world so Tottenham have to prove they're the club he can lift trophies at.”
While expecting Kane to stay put, Waddle is concerned by the interest being shown from Real and La Liga rivals Barcelona in Christian Eriksen.
He added on a key creative influence: “If Tottenham let Eriksen go, they won’t be able to replace him.
“He is a top player who anyone would be interested in signing and if Tottenham want to be seriously competing against the top clubs these are the types of players they need to keep hold of. Eriksen is vital to the club, especially as they move into their new stadium.
“Eriksen will know what he is worth and he is within his rights to demand it. Tottenham have had a lot tighter budget moving in to the new stadium and it would be a lot cheaper to give Eriksen what he wants than to go a spend a large sum of money trying to replace him.”
Another of those to have seen a move away from Spurs mooted is head coach Mauricio Pochettino, with the Argentine having attracted interest from Madrid and Manchester United.
“Daniel Levy will give Pochettino what he wants to stay at Tottenham and make them genuine title contenders,” said Waddle.
“Pochettino could virtually walk in to any vacant manager role and Tottenham know that he will leave unless they make the funds available for him to sign top players and progress the club.
“Tottenham know how important it is to keep Pochettino at the club and they will have showed him the club's plans for the future. He's clearly a massive part of it and will have a massive say in it. It's an exciting time at Tottenham and he'll want to be a part of that.
“Pochettino wants to win trophies, but he's got a long career ahead of him which means he has time to create the dynasty he's started at Tottenham. If Tottenham fail to compete and win trophies, then he'll be tempted by the offers that come his way.”