Tottenham have endured the worst possible start to the 2026/27 Premier League campaign.
Tottenham Hotspur have endured a nightmare start to the campaign under Roberto De Zerbi and sit bottom of the Premier League after their first five matches. They remain one of just three sides yet to taste victory this term alongside Bournemouth and Fulham.
That’s despite a huge summer revamp at White Hart Lane with more than £300m being spent on new recruits, as they look to kick on after back-to-back 17th place league finishes. Their first league goal did not arrive until matchday five, with Conor Gallagher and Jan Paul van Hecke scoring in the 3-2 defeat to Aston Villa before the international break.
Former scout thinks Tottenham will look to move on two players in the winter transfer window
Conor Gallagher has been one of the players who has been in and out of Roberto De Zerbi’s side. He has struggled for regular minutes this season, alongside James Maddison, as De Zerbi attempts to find the right balance in his side and winning formula.
James Maddison, on the other hand, has been still building up his fitness after suffering an ACL rupture on his right knee last year. The creative midfielder has now returned from a slight shoulder injury, but he has not yet managed to bulldoze his way into De Zerbi’s XI.
While there have been improvements in certain aspects of Tottenham’s play, one issue that still needs sorting out is the creativity. With Gallagher unconvincing, Maddison still not fully fit, and Dejan Kulusevski on his comeback trail from a serious knee injury, summer signing Mateus Fernandes currently occupies the No.10 role.
Now, ex-scout Bryan King has tipped Gallagher and Maddison to leave Tottenham in the January transfer window.
“I look at Gallagher and Maddison, and they’ve been used as substitutes, or Gallagher’s been used more than Maddison as a starting player,” Bryan King exclusively told Football Insider.
“I think they’ve got to start looking at the situation. One of those players is going to have to be looked at probably to leave in the January window. You can’t keep those two, and you’ve got Kulusevski coming back, so something has got to happen there.
“Personally, I’d look at Maddison because I know he hasn’t been starting. He’s a player that I would be thinking, if De Zerbi is going to be allowed to stay in the job, he’s a player that he doesn’t really fancy.”
De Zerbi will want to keep his squad intact
It is very early to determine who the Tottenham boss decides to keep and move on when the transfer window reopens. De Zerbi knows the importance of squad building, and having made some brutal decisions during the summer, he will try to keep his roster intact.
So, unless players show up on his door and ask to leave, the Italian tactician ideally would want to extract the best out of the current group and challenge for European spots.
