Middlesbrough flop part of ‘disastrous’ £50m transfer window in exile as contract terminated

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Middlesbrough have been trying to secure promotion to the Premier League since their ill-fated relegation in 2016/17.

Once an established Premier League club, it’s now been eight years since Boro have graced the top flight of English football.

Middlesbrough spent just one campaign back in England’s premier division under Aitor Karanka, who was sacked in March 2017 with the club firmly in a relegation battle.

Results did not improve upon his departure, however, and the Teessiders went down along with rivals Sunderland and Hull City.

Boro have come close to securing a return to the Premier League, finishing in the play-offs twice and seventh on two occasions, but their efforts have been in vain, in no small part due to several years of questionable recruitment.

• READ MORE: Middlesbrough stance on Hayden Hackney summer transfer revealed as Crystal Palace and Fulham ‘doing their work’

Middlesbrough flop Britt Assombalonga has contract terminated

Fans of the North East outfit became very accustomed to poor recruitment prior to Kieran Scott’s arrival, and even in 2024/25, club legend Bernie Slaven has slammed Middlesbrough for their January signings.

While the most recent window was not great, it still wasn’t anywhere near as bad as the summer of 2017.

Boro signed 11 senior players, spending, as per Hartleepool Mail, somewhere in the region of £50m.

Barring Jonny Howson, who is still currently plying his trade at the Riverside Stadium, and perhaps Darren Randolph for a period, all of those additions proved to be a huge waste of money.

This dire spending led former manager Tony Pulis to claim in 2020 that ‘the window Middlesbrough had before I joined was probably the most disastrous one that the football club have ever had.’

One of the biggest disappointments from that nightmare window was Britt Assombalonga, who had scored 30 goals and assisted two in 69 matches for Nottingham Forest before making the move to Teesside.

After failing to replicate that form with Boro, their record signing eventually left the club on a free transfer in August 2021 for Adana Demirspor.

He then had a spell with Watford before two more stints in Turkey, most recently lining out for Amed SK.

However, after less than a year with the Turkish outfit, Assombalonga had his contract terminated in February 2025 and has been unable to find a new club since.

Middlesbrough record signings

Eight years on, Assombalonga remains Middlesbrough’s most expensive signing, taking the place of another centre-forward who flopped in the North East, Afonso Alves.

But barring the aforementioned duo and perhaps Jordan Rhodes – though his limited goal contributions were key to Boro winning promotion in 2015/16 – the Reds’ most expensive signings have, for the most part, had solid careers in the North East.

Fabrizio Ravanelli is one of the most talented players to ever line out for Boro, while Gareth Southgate and Ugo Ehiogu played key roles in the club’s League Cup triumph of 2004 and in Middlesbrough reaching the UEFA Cup final two years later.