Middlesbrough backed to eye £0 Ross Stewart transfer but 'red flag' raised | OneFootball

Middlesbrough backed to eye £0 Ross Stewart transfer but 'red flag' raised | OneFootball

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Football League World

·16 June 2026

Middlesbrough backed to eye £0 Ross Stewart transfer but 'red flag' raised

Article image:Middlesbrough backed to eye £0 Ross Stewart transfer but 'red flag' raised

FLW's Middlesbrough fan pundit has given his verdict on a possible move for Ross Stewart

Middlesbrough are preparing for another year in the Championship after suffering disappointment in the play-offs.


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The Teesside outfit lost to Hull City in the final, with a stoppage time goal from Oli McBurnie separating the two teams.

Kim Hellberg will be aiming to lead his team one step further in 2027, with the club setting their sights on promotion back to the Premier League.

Boro haven’t competed in the top flight since 2017, but they will be targeting a top two finish next year potentially.

It could prove a busy summer ahead at the Riverside, particularly as this will be Hellberg’s first chance to oversee pre-season since taking over last November.

The Swede will be keen to strengthen the squad in a bid to bolster their chances of fighting at the top of the Championship again in the next campaign.

Middlesbrough issued Ross Stewart free transfer warning

Article image:Middlesbrough backed to eye £0 Ross Stewart transfer but 'red flag' raised

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When asked if one option for the club this summer could be Ross Stewart, FLW’s Middlesbrough fan pundit Liam Day claimed that he should be considered but his wages could prove a stumbling block to a deal.

He believes the forward’s injury record also presents a red flag, but that he could be someone that offers the team something different in attack, as they saw up close in their play-off semi-final against Southampton.

“I definitely think that’s an option Boro could consider, and maybe should consider,” Day told Football League World.

“I think the injury record is probably the biggest red flag, and then probably the wage demand.

“If Southampton can’t agree wages with him then he must be asking for something big.

“I don’t know if he’s proper Hellberg’s style, but I think we’ve been missing someone who can win headers in the box and do what he did in the play-offs, score that goal.

“So, it’s definitely one that Boro could consider, but I think wages might be a big, big stumbling block if he can’t agree with Southampton, who have realistically have a Premier League budget for stuff like that.

“Then it could be a big issue for us.

“But it’d be an option on a free, you can sort of save money in that sense, so I think Boro should consider it, really.”

Stewart departed Southampton at the end of the campaign, with his contract expiring this month.

The forward endured a lot of injury issues during his time at St. Mary’s, making just 53 league appearances in four seasons with the Hampshire outfit.

However, he made 25 appearances this campaign, contributing eight goals and two assists for the Saints as they finished fourth in the table.

The Scot is a free agent, and will be looking for his next club after being unable to come to an agreement on a new deal with Southampton.

It remains to be seen what kind of business Middlesbrough will complete, with the market opening on Monday.

A lot of their activity may yet depend on the future of Hayden Hackney, who is being linked with a big money move to the Premier League.

It’s been claimed that Boro are seeking £25 million in order to cash in on the midfielder, and that could dictate their next steps if that comes to fruition.

However, Stewart’s free agency means any cost of a deal would be relatively low.

Article image:Middlesbrough backed to eye £0 Ross Stewart transfer but 'red flag' raised

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Ross Stewart could be an option for Middlesbrough

While his potential wage demands and his fitness record are both red flags, there’s no denying someone like Stewart could be a smart option.

The 29-year-old has shown that he can consistently score at this level when available, and that is extremely valuable.

Goals weren’t necessarily the problem for Boro, but their dip in form that cost them a top two spot came when they hit a rough patch in finding the back of the net.

So it would make sense to bolster their front-line, and Stewart being available as a free agent will make him an appealing option.

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