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The dilemmas facing Chris Wilder this summer transfer window at Middlesbrough



Middlesbrough had a good season under the management of Chris Wilder but will have been disappointed not to have finished in the top six after taking it to the final day.

Despite coming close to finishing in the play-offs, a 4-1 defeat against Preston on the last day of the Championship season meant Boro ended the year five points away from where they wanted to be.

Therefore, we can see that the side are close but there is also still some work to be done over the summer if they want to go a step further next season.

With that in mind, here we take a look at the dilemmas that are facing Wilder at the Riverside in the upcoming window…


If Wilder wants his side to solidify a spot in the top six next season, he will have to look to bring in a consistent goalkeeper.

This season Joe Lumley lost his place in the starting line-up with Luke Daniels stepping up but the Boro boss will be hoping to secure a permanent solution.

The club have been linked with Newcastle United’s Karl Darlow which would be a solid signing as he is a goalkeeper with Championship and Premier League experience having won promotion to the top flight with the Magpies back in 2017.

However, Middlesbrough won’t be alone in their pursuit for the 31-year-old’s services with fellow Championship side West Brom also interested as well as Manchester United, who are keen to do a swap with him and Dean Henderson.

Furthermore, with Darlow still under contract at Newcastle, this is a deal Boro have to fork out for leaving Wilder with the question of how far he pushes for this move before considering alternative options.

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Ross Stewart

Another player Boro has been linked with this summer is Sunderland’s Ross Stewart after his brilliant season in League One, which saw him find the net 26 times – making him the division’s top goal scorer.

Currently the striker has just a year left on his contract with interest incoming from Wilder’s team, Sheffield United, QPR and Rangers according to The Mirror (26th May, page 62).

However, Black Cats sporting director Kristjaan Speakman recently confirmed the club were going to speak to their player about a new contract.

Regardless of whether or not he signs that though, you can imagine Sunderland will be asking for a decent fee for the 25-year-old, especially following their promotion to the Championship this season.

Therefore, this is another one Wilder needs to weigh up and decide how far he wants to go for this deal.

Jonny Howson 

Boro’s captain has had a big part to play in the team this season having made 45 appearances, scoring one goal and contributing an assist.

The 33-year-old is out of contract at the Riverside this season but the side has confirmed that they have offered a fresh deal to the player.

However, there has not yet been an update on whether this deal will be accepted by Howson leaving the club with a sense of uncertainty as it stands.

Everyone at the club will be hopeful this is one they can get over the line but Wilder may also have to start thinking about replacement options if a deal isn’t agreed soon.

Passionate football fan. Currently studying a masters at UCFB alongside writing for Football League World.

ScoopDragon Football News Network

Article title: The dilemmas facing Chris Wilder this summer transfer window at Middlesbrough

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