The club hope to proceed in a manner that sees them complete a deal for an attacking midfielder in the next week.
We recently revealed on Flashscore how the Asia pre-season trip could become a farewell tour for Son - and that became a reality when he announced that he is preparing to leave the club.
Son played his final game on Sunday - ahead of a proposed move to Los Angeles - and news of a club icon leaving is always difficult to bear, even though it has been expected.
They are now contemplating a potentially serious knee injury to Maddison too, from later in the same game versus Newcastle, and it puts the spotlight on their transfer activity even further.
Mohammed Kudus has joined for £55million and Joao Palhinha is moving in on loan - but Spurs missed out on another leading target in Morgan Gibbs-White and need new creative talent through the door.
Among the targets is Stuttgart attacking midfielder Enzo Millot. He is one of the names they have been considering in recent weeks, though there is competition for his signature from some other top European clubs - including Atletico Madrid.
Tottenham have also considered Manchester United’s Kobbie Mainoo while Bilal El-Khannouss has been weighing up his future in the past week and Spurs are also in the picture.
Leeds and Aston Villa are among clubs that have been enquiring about the Leicester City player, but his creative spark and ability to find space in dangerous positions is something that very much appeals to Tottenham too.
Spurs want to ensure they are not caught up in bidding wars in order to get good value deals. That notion has become more difficult now that selling clubs know they are in a position where they need to make a signing.
They have also contemplated an elite star, including Xavi Simons of RB Leipzig.
Eberechi Eze has a release clause at Crystal Palace that could be met and they have been encouraged to make contact very soon if they want to trigger it.
The club have continued to scour the market with players such as Liverpool’s Harvey Elliott also informally explored as they seek a solution.
In advanced positions they have also considered a flair player - such as Jack Grealish and Alejandro Garnacho - and sources do believe it is likely they end up signing another player with game-changing ability in that wide area.
This is a key stage of the summer as Spurs attempt to be fully prepared for the new season.
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