As Middlesbrough embark on another Championship play-off push in 2025/26, EFL Analysis understands two Chelsea players are of interest to the Teessiders.
After failing to finish in the top six, Middlesbrough recently sacked Michael Carrick, marking the end of almost three years in the dugout at the Riverside.
Middlesbrough are set to appoint Rob Edwards as his replacement. Supporters are underwhelmed by this decision after being sacked by Luton Town in January, with the Hatters eventually suffering relegation to League One.
EFL Analysis exclusively revealed that Steve Cooper was Boro’s first choice, though as his wage demands were too high, they quickly moved on from the Welshman, handing Edwards the opportunity.
Edwards will be unveiled as Middlesbrough’s manager on Thursday, and already, there are multiple players being linked with a move to the Championship side.
Alfie Gilchrist during Sheffield United clash against Hull City
Photo by James Gill – Danehouse/Getty Images
Middlesbrough eyeing Chelsea duo Josh Acheampong and Alfie Gilchrist
One of the biggest problems facing the new manager is resolving their right-back issue. Anfernee Dijksteel has left Middlesbrough as a free agent with his contract expiring on June 30, and Luke Ayling could depart in the summer window, potentially leaving them with zero senior right-back options.
That is why EFL Analysis can inform, via football correspondent Graeme Bailey, that Middlesbrough have previously ‘inquired’ about Chelsea right-back Alfie Gilchrist, while Josh Acheampong is another on their radar, though the chances of him dropping to the Championship are slim.
“He’s one [Gilchrist] who Middlesbrough have inquired about previously. They also asked about Josh Acheampong, but I don’t think he will come to the Championship,” Bailey said.
“We have discussed previously how much Middlesbrough want a right-back, especially if Luke Ayling goes as well as Dijksteel. They will probably want two; they just do not have the back up right now.
Boro aren’t alone in their admiration of Gilchrist, though, as Sheffield United and other Championship rivals want him too.
“There’s plenty of interest in Gilchrist from what I’m hearing,” Bailey added. “Sheffield United obviously stayed down and he did well there, so I wouldn’t rule them out.
“He’ll get himself a move, but it’s early days. There are certainly a number of options for him, and I think it probably will be a permanent deal. He will be a solid signing for someone.”
What John Terry once said about Gilchrist
Boro ideally need to sign two right-backs, preferably someone experienced if Ayling leaves, and a younger player to challenge.
Gilchrist, who spent the 2024/25 campaign on loan at Sheffield United, is someone who can slot in as a right-back or centre-back, making him perfect for the system Edwards typically deploys.
The 21-year-old supplied two assists in 30 Championship appearances last term, and with Chelsea willing to sanction his exit, Boro could be getting an unbelievable talent.
That is an opinion shared by John Terry, who compared the attitude and intensity of Gilchrist to the type of player he was.
“Literally from the first training session in which I saw him, he reminded me of myself,” Terry told the Daily Mail in November 2024.
“He was keen to learn, asking me questions about defending and constantly picking my brains over what I would do in different situations.
“And he’s 100 per cent in everything he does. Whether that’s the warm-up to get him going, he’s all-in. You don’t ever want to take that away. Even on his recovery days, he’s 100 miles per hour.
“As he gets older, he’ll understand how to manage that and how to be. But it’s a great trait to have for a young player and it can certainly set you apart.”