Tottenham Hotspur head into the North London derby against Arsenal on Sunday with four points from their opening three Premier League matches.
Former Premier League manager Sherwood believes that if Spurs start 'losing players' and then they fail to replace them with 'better players' then the likes of Alli and Kane will walk out of the door with them.
After Spurs' defeat to Newcastle last Sunday, Mauricio Pochettino claimed that his squad is 'unsettled' with the futures of a number of his star players up in the air, as reported by Sky Sports.
Speaking to BT Sport Score's official Twitter account, Sherwood stated that there's 'no better way' for Tottenham to lift their recent gloom by beating Arsenal in the North London derby.
"They're going to be rich boys when they finish their careers," Sherwood told BT Sport. "But how many medals they got? That's why they do that.
"That's why they are going to lose Christian Eriksen. Not because he wants to earn more money somewhere else. The club he will leave for will be the club he feels has a better chance to win something. And that's the reason. Vertonghen will be exactly the same. Alderweireld's a little bit different, but he's running his contract down.
"If they start losing players of that quality and not replacing them with better players then you start losing your top players like Harry Kane and Dele Alli. And, at the moment, there's a little bit of a cloud hanging over Tottenham, but there's no better way of lifting that by winning a North London derby and they're capable of doing that."
Eriksen has only started one Premier League match for Spurs this season, and for the other two, he came off the bench.
It remains to be seen what happens against Arsenal because Spurs need a player of his quality in the middle of the park if they are to pick up any points.
Jan Vertonghen is another player who hasn't featured this term and given Spurs' defensive problems, he also needs to return to the starting XI for the North London clash.
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