James Maddison spotted with Tottenham target at Wimbledon as Levy chases new number six

Originally posted on To The Lane And Back
By Jainil Shah | Last updated Jul 22, 2025 8:31 AM ET

James Maddison spotted with Tottenham Hotspur target Conor Gallagher

Tottenham Hotspur and Daniel Levy are compounding on their transfer activity in the ongoing summer transfer window, and if we go by the recent Wimbledon sighting complemented by the rumours in the transfer mill, it may have dropped a major hint.

The North Londoners have already got their hands on Mohammed Kudus and Takai this offseason, whilst the lawyers at Hotspur Way continue to fight to get their hands on Nottingham Forest midfielder Morgan Gibbs-White this summer, but that is not all. But Daniel Levy is still working on bringing in more key additions for Thomas Frank this summer, with a midfielder and centre-back possibly now on the list at N17.

And now we have seen Atletico Madrid midfielder Conor Gallagher hanging out with James Maddison and that so in the middle of the transfer window.

Conor Gallagher and James Maddison double up at Wimbledon

Gallagher has been subject to links with a move to Tottenham for quite a while; in fact, the North Londoners were right in the think of things when the England international moved to Atletico Madrid, and now the club have reiterated their interest in him despite his recent move to Atleti. And he was spotted sitting with Maddison on Centre Court at Wimbledon on July 6, where the two were there to watch Carlos Alcaraz, and if we look at this from the Lilywhites supporters point of view, let’s be real, this one was not just a casual day out.

Sources say that like Postecoglou, Thomas Frank is also a big fan of Gallagher, and Tottenham are again seriously considering a move for him. Premier League heavyweights Newcastle are also in the frame for his signature, but the chance to return to London and possibly reunite with his England teammate and Wimbledon seat partner Maddison could give Tottenham a big edge in the midfield.

Atleti took away Johnny Cardoso from Tottenham’s grasps earlier this summer, but that means that Gallagher’s minutes will be affected, which opens the doors for the North Londoners.

Gallagher is not the only midfielder that Tottenham are considering

Conor Gallagher is not the only number six Tottenham are looking at, as the North Londoners are also talking with Joao Palhinha, where personal terms aren’t expected to be a problem. Though Bayern want around £30m for the former Fulham midfielder, Levy is willing to shake hands for something closer to £20m. And another former Premier League maestro in Douglas Luiz is also being considered by the chiefs at Hotspur Way. The Brazilian has struggled at Juventus and wants to move back to the English top tier this summer.

This article first appeared on To The Lane And Back and was syndicated with permission.

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