Daniel Levy and Antonio Conte contemplated trying to sign Cristiano Ronaldo last year before ultimately deciding against making a move for the then Manchester United star.
Ronaldo's relationship with United broke down after a fine return campaign with the Portuguese seeing his role diminished under new manager Erik ten Hag.
It became clear that the footballing icon was looking to find his way to a new club and ideally one that was in the Champions League.
And Sportsmail's Ian Ladyman has revealed that Tottenham were one of the clubs that thought about making an approach.
Levy will often sit at the coach's table in the canteen at the Spurs training ground.
And it was here that he and Conte pondered the idea of brining in one of the biggest names in the history of the game.
The duo, on much better terms back then, agreed that it wasn't the right move for the club.
Ronaldo would go on to sign for Saudi Arabian side Al-Nassr, becoming the most highly paid player in the world.
Conte left Tottenham by 'mutual consent' following his extraordinary rant after the 3-3 draw with Southampton in the team's last Premier League outing.
Conte took aim at all areas of the club, from players to ownership, leaving his position untenable.