Bailly, 24, was Jose Mourinho's first signing as Manchester United boss in 2016, luring him away from Villarreal in a deal worth around £30million having starred in Spain.
The Ivorian international has suffered some injury problems during his time at Old Trafford, and now find himself out of favour after a difficult start to the season.
Bailly has started just one league game since the end of August, and that came in the 3-2 win over Newcastle United, in which Bailly was substituted before half time.
The centre back appears to be edging towards the exit door, and The Sun report that Bailly will hold showdown talks with United this week in order to decide whether he will be moving on in January.
Spurs are looking for younger centre backs to eventually succeed Jan Vertonghen and Toby Alderweireld, and Bailly would certainly bolster Pochettino's options, alongside Davinson Sanchez and Juan Foyth.
However, United are unlikely to be open to selling Bailly to a direct rival, and Tottenham face a battle to reunite Pochettino with Bailly – even if United do decide to let him go in January.
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