Chelsea, Arsenal or Milan? Dean Henderson at Man Utd crossroads

David Lynch
David Lynch
  • Updated: 24 May 2021 13:39 BST
  • 4 min read
Chelsea, Arsenal or Milan? Dean Henderson at Man Utd crossroads

With just two games of Manchester United’s season remaining, Dean Henderson’s future at the club is less clear than ever.

Having returned from a successful two-year loan stint with Sheffield United over the summer, the 24-year-old faced a slow start to his first campaign with United’s senior squad.

But sporadic cup appearances were replaced by consistent Premier League starts in early March, with Ole Gunnar Solksjaer having seemingly decided to ditch David de Gea.

Unfortunately for Henderson, mistakes in last week’s defeat to Liverpool were punished with a place on the bench for the subsequent visit of Fulham to Old Trafford.

And, as Solskjaer later explained, neither man has yet locked down a starting place in the upcoming Europa League final against Villarreal.

The Norwegian said: “It was David’s turn to play now. Of course, he’s played in Europe, Dean has played most of the league games, so for me to have two keepers ready for the final is important.

“It’s up for grabs [Europa League final place], of course it is, I will make up my mind after these two league games.”

Henderson has made no secret of his willingness bring a 10-year stay at Old Trafford to an end if he is not a regular in the first.

So, should De Gea get the nod against Villarreal, where might the Englishman’s future lie? Here, we assess the options.


In their desperation to take £70m Kepa Arrizabalaga out of the firing line, Chelsea signed Edouard Mendy from Rennes over the summer.

But, while the Senegal international has fared well enough, it is believed that he is little more than a stop-gap for the Blues.

Chelsea, Arsenal or Milan? Dean Henderson at Man Utd crossroads

Chelsea, Arsenal or Milan? Dean Henderson at Man Utd crossroads

AC Milan’s Gianluigi Donnarumma had been linked with a switch to west London as he nears the end of his contract, but Juventus have recently emerged as frontrunners.

So, if Chelsea remain committed to moving on Arrizabalaga and demoting Mendy, Henderson could well be viewed as a strong alternative.

The 24-year-old would surely jump at the chance to remain in England with another Champions League regular.


With Donnarumma’s contract days from expiring, it seems unlikely that he will sign an extension to stay with Milan.

As such, it seems the Italians are set to be in the market for a new goalkeeper when the summer transfer window opens.

Competing with Premier League clubs in terms of wages might be difficult, but the allure of playing for a traditional European giant would surely appeal to Henderson.

And, should Milan get over the line in their chase for the Champions League in the coming days, this move would be a lot easier to imagine.


Arsenal also face some uncertainty regarding their goalkeeping situation ahead of the summer.

Bernd Leno‘s contract will be two years from expiry when the season comes to a close and the German hasn’t ruled out a possible departure.

He recently said: “I’m very happy at the club. I don’t know what will come in the future, but I’m open to everything. Maybe for a new adventure or to stay at Arsenal.”

Chelsea, Arsenal or Milan? Dean Henderson at Man Utd crossroads

Chelsea, Arsenal or Milan? Dean Henderson at Man Utd crossroads

Should a decent offer come in, the Gunners will have the opportunity to future-proof between the sticks by bringing in the young and hugely talented Henderson.

And, unlike in previous years, Manchester United would probably have no qualms about strengthening an Arsenal side that have struggled to get near them this season.

Leeds United

Guaranteed a top-half finish on their return to the Premier League, Leeds United look like they are here to stay.

But Marcelo Bielsa is sure to want to kick on after such an encouraging campaign, and there is potential for improvement between the sticks.

Signed permanently from Lorient last summer, Illan Meslier became the first goalkeeper under the age of 21 to keep eight clean sheets in a Premier League season.

But Bielsa has also had to defend the Frenchman from criticism at times, and his relative inexperience is a concern for a side who wish to kick on.

Signing Henderson from their old rivals Manchester United could be one possible route to strengthening in that area.