How Middlesbrough now feel about Hayden Hackney dilemma as ‘realistic’ transfer outcome mooted

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The future of Middlesbrough midfielder Hayden Hackney hangs in the balance, and EFL Analysis can exclusively reveal the internal thoughts at the Riverside on the transfer saga.

Middlesbrough have made an impressive start to the 2025/26 Championship under new manager Rob Edwards.

On opening weekend, Middlesbrough beat Swansea City 1-0 thanks to a 51st minute goal from defender Dael Fry.

Most recently in the league, Boro won 3-0 at Millwall in a resounding victory courtesy of goals from Hayden Hackney, summer signing Alfie Jones, and Delano Burgzorg.

Hackney’s goal broke the deadlock at The Den amid the uncertainty regarding his footballing future, and EFL Analysis can now reveal the internal thoughts at Boro on their homegrown star after his talks with Ipswich Town.

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Exclusive: How Middlesbrough now feel about Hayden Hackney

Throughout the summer transfer window, Hackney has been expected to depart his boyhood club.

After Middlesbrough agreed a deal in principle for Hackney with Ipswich, reports emerged that Hackney turned down Ipswich’s offer after holding talks with Tractor Boys officials.

The England youth international played the full 90 minutes in both wins over Swansea and Millwall despite the uncertainty regarding his future with transfer deadline day less than two weeks away.

Now, EFL Analysis can exclusively reveal, with information from our Chief Football correspondent Graeme Bailey what the “realistic” outcome is for Middlesbrough regarding Hackney’s future.

Bailey explained: “Boro are open to a deal is the wrong word, but they do realise that they’re susceptible to Hackney offers late on and they can’t rule anything out there.

“Especially, I think, with the Premier League, the clubs who have a bad start in the Premier League, who suddenly look for options around there.

“Boro always thought clubs would come late for him. There’s a real belief that Hackney will still go.

“I think it’s going to be hard for Middlesbrough to reject some big offers that come in. There’s a real chance that two, three, or four clubs could yet come in with an offer there.

“I think Boro have done the Sverre Nypan deal (loan from Manchester City) to cover themselves a little bit. It’s pretty sensible that they’re doing that.

“But I believe Boro need to get rid of a few for the 25-man squad rules, which Nypan will count in as he’s on loan. So that is an interesting element.

“I think Hackney and probably Tom Glover will go. And then that will free Boro up to sign another striker.

“I don’t think fearful is the word for the Hackney situation, Boro are just being realistic.

“They know that they’re going to get offers in these final two weeks, it just depends on how big they are and whether the player wants it, but I think it’s still going to be very hard for Boro to keep him.

“The fact that he played well last week obviously helps the team, but it also doesn’t help Boro’s quest to keep him.”

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Middlesbrough and Ipswich Town transfer moves after Hayden Hackney saga

After missing out on signing Hackney, the Tractor Boys have turned their attention to Premier League loan moves.

Following Ipswich’s rejected loan bid for Lewis Miley of Newcastle United, reports recently emerged that Ipswich want Phillip Billing on loan from Bournemouth after he helped Napoli to the Serie A title on loan last season.

On Teesside, the Riverside hierarchy completed their fifth summer acquisition with Middlesbrough’s loan signing of Sverre Nypan from Manchester City.

In Nypan’s first interview as a Boro loanee, the Norwegian starlet, who was signed by City for £12m this summer, explained that he is a “pretty physical, but mostly technical” player.

Given the central midfielder’s resemblance to Hackney in terms of playstyle and profile, his season-long loan to Middlesbrough would help soften the blow if the in-demand boyhood Boro fan is snapped up by Premier League suitors.