Spurs signing, two Aston Villa transfers among six most bizarre PL deals in 2026 January window

The transfer activity (or lack thereof) this January has stuck to the same theme as recent winter windows, which have also been dull non-events.

You have to clutch at straws to pick out standout moments from this January transfer window, but there have thankfully been some bizarre deals to catch the eye.

So, here are six of the strangest Premier League transfers of the 2026 January window, which are also polar opposites to James Ward-Prowse to Burnley, which is surely the most obvious deal in any window ever…

Oscar Bobb – Manchester City to Fulham

This feels like it could prove to be a pre-Chelsea transfer for Bobb, who could follow the same path as Cole Palmer to make Manchester City look rather foolish.

Bobb’s ceiling is certainly not as high as Palmer’s, but it still feels like he has untapped potential that Man City could have benefited from had he retained their backing.

Still, Man City will view his exit as a risk worth taking, with this being the latest of many examples of Pep Guardiola’s side selling really well. £27m is a huge fee for a player who has only made 13 Premier League starts.

READ: The biggest transfers in the world in the 2026 January transfer window

Facundo Buonanotte – Brighton to Leeds United

Better late than never, I suppose…

A move to Leeds United was in the pipeline in the summer for Buonanotte, and this would have been ideal for both parties after he was one of Leicester City’s better players last season. But the attacker joined Chelsea instead in a deal which, even by their lofty standards, was particularly pointless.

Buonanotte is certainly a good Premier League player, but he was never likely to feature regularly for Chelsea at this stage of his development, and this proved the case in the first half of the season despite impressing in flashes.

It initially felt likely that the next steps for Buonanotte would be a permanent move to Chelsea en route to a profit sale for BlueCo. Instead, he has had his Stamford Bridge dream taken away by having his loan terminated before joining Leeds for the remainder of the season.

Buonanotte and the clubs involved have finally stumbled on the right outcome for everyone concerned, but it took some unnecessary faff to get there.

Conor Gallagher – Atletico Madrid to Spurs

Robertson to Spurs is way more left-field than the Gallagher signing, but this one does not make perfect sense either.

Gallagher was always likely to be on the move in this window as he had dropped in the pecking order at Atletico Madrid and will have his eye on snatching a place in Thomas Tuchel’s World Cup squad, but he would not have expected to be involved in a permanent deal or a hijack.

Given Atletico’s lofty demands, a loan-to-buy deal seemed Gallagher’s most likely route back to the Premier League and this is what Aston Villa were offering until Spurs came bounding in with an irrefutable £34m permanent bid.

The finances on the table and the lure of a return to London gave Villa no chance, while Spurs ease their midfield issues with the signing of a former foe from down the road. On the face of it, this is a solid signing for the north London outfit, but the drastic manner in which they went about signing him reeks of desperation.

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Pascal Gross – Borussia Dortmund to Brighton

One of this window’s most wholesome transfers is also one of the most bizarre, with 34-year-old Gross unexpectedly returning to Brighton only 18 months after leaving for Dortmund.

The midfielder racked up 261 appearances for Brighton during his first spell at the AMEX Stadium, and his upward move to Dortmund was certainly well-deserved, but it did not quite pan out as he intended.

Limited game time in a World Cup year led to his second spell at Brighton, and there has already been evidence of this being a beneficial move for player and club. A really nice story that no one saw coming.

Donyell Malen – Aston Villa to AS Roma

Before Robertson and/or Luiz steal his thunder, Malen is currently at the heart of this window’s oddest Premier League transfer.

We, like many others, initially laughed off reports suggesting Malen could head to Roma because he’s been rather important for Aston Villa this season and they are not exactly spoiled for choice in attack.

But this transfer became serious rather quickly and was even finalised way before the Villans had a replacement lined up, which did leave Unai Emery’s side at risk of having egg on their face.

But, in the end, it’s all well that ends well as Malen gets a good move and Aston Villa are replacing him with a cheaper alternative who is a proven Premier League goalscorer. 

Evann Guessand – Aston Villa to Crystal Palace

Palace have had a really torrid time this month and the arrival of Guessand will hardly improve their mood.

With Jean-Philippe Mateta likely heading to AC Milan, Palace needed to sign a striker to replace the exit-bound forward and have opted to go for an Aston Villa flop.

24-year-old Guessand initially reportedly caught Palace’s attention after he grabbed 12 goals and seven assists for OGC Nice in 2024/25, but he failed to score in his 13 Premier League games for Aston Villa and was generally ineffective.

The possibility of Palace paying £50m to sign Jorgen Strand Larsen is bizarre too, with it currently hard to see either player being a sufficient replacement for Mateta.

READ NEXT: Every Premier League deal completed in the 2026 January transfer window