Middlesbrough will wish they broke Sunderland hearts with ambitious Man Utd deal: View | OneFootball

Middlesbrough came close to securing a Championship play-off spot last season but they would ultimately fall short of achieving their top-six aspirations.

Michael Carrick's first full season as Middlesbrough boss was one of significant transition as Boro had stacked up on loan players the previous year, in an attempt to end their Premier League exile.

Ryan Giles, Rodrigo Muniz, Cameron Archer, Aaron Ramsey, and Zack Steffen were among those faces that returned to their parent clubs at the end of the 2022/23 campaign, one that left Carrick's squad requiring a sizeable overhaul last summer.

But despite a poor start to the season, Boro eventually found their rhythm as the season progressed, and as Carrick's side began their ascension up the table, the January transfer window gave them the opportunity to add the final pieces to a squad that could get the club over the line.

One such player that was reportedly on Boro's radar was Manchester United and former Sunderland winger Amad Diallo.

Boro were in for Amad

Reporting via his Patreon, journalist Alan Nixon revealed that Middlesbrough were leading the race to sign the United wideman last January, as Carrick looked to add the former Sunderland sensation to his ranks.

Nixon reported that Boro had offered United the best financial package, with the club being willing to contribute the most amount of money to the Ivorian's wages in what would've been a loan deal.

The report stated that the Teessiders were hopeful of securing an agreement with the Red Devils imminently, as their offer was considerably better than those from other interested clubs.

Ultimately, a deal would not materialise for the highly talented winger, with Diallo opting to remain at Old Trafford.

In what would become an iconic moment for Sunderland fans, Diallo took to his Instagram account to rubbish rumours of a potential move to Teesside, as he posted a picture of him wearing a Sunderland shirt with a kissing emoji.

That post, along with Diallo's exploits at the Stadium of Light during the 2022/23 season have cemented his place in Sunderland folklore, as the winger quickly became one of the most popular Black Cats players in recent times.

As such, seeing Diallo wear the Middlesbrough crest on his chest would've been a heartbreaking sight to witness for Sunderland fans, and although it wouldn't have completely tarnished his legacy on Wearside, it certainly would've been a lingering stain.

His 14 goals and three assists during his season in the North East also make him one of the finest loan signings the Championship has seen in many a year, and it was no surprise to see Boro being desperate to acquire his services.

Amad's arrival could've made the difference

Certain players are defined as match-winners, and Diallo certainly proved that he falls into that category during his time with Sunderland, and he's doing it again at Manchester United.

Middlesbrough fell four points short of the top six last season, and it's not controversial to say that the 21-year-old could have won those points for Boro in the second half of the season.

Carrick's squad lacked creative threat from wide areas in 2023/24, with the likes of Riley McGree, Marcus Forss, and Isaiah Jones all missing chunks of the campaign with injury problems.

This largely left the likes of Sammy Silvera and Sam Greenwood to try and fill that void, something which they were largely unable to do.

And so the presence of Diallo on the flank could well have taken Middlesbrough's attacking force to the next level, and helped turn those frustrating draws into wins, and disappointing defeats into vital points.

The winger now looks set to play a big part in United's future, as he took the chance offered to him by Erik ten Hag last season.

Middlesbrough and Carrick have clearly identified that position as a weak spot that needed addressing this summer, however, and have moved quickly to sign ex-Huddersfield Town loanee and versatile forward Delano Burgzorg from Mainz.

But there may still be tinges of regret that they weren't able to land Diallo to aid their promotion push and break Sunderland hearts in the process.