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Middlesbrough are one of the most historic clubs in England, boasting a rich history that includes lifting the League Cup and featuring in a UEFA Cup final.
Over the years, they have made a number of significant signings to reflect their ambition and past successes.
However, the club is currently in the Championship, having not featured in the top flight since 2017, and are working on a tighter budget than they have done previously.
While newly appointed manager Rob Edwards would likely love to make several transfers during this summer window, it is more likely that he may suffer the same fate as previous Boro managers.
Boro came close to the playoffs last season, and a few big transfers may be what they need to get over the line.
EFL Analysis revisits the club’s most expensive-ever signings ahead of next season.
The top five most expensive Middlesbrough signings
5. Martin Braithwaite
Martin Braithwaite joined Middlesbrough as a centre-forward in the 2017/18 season from Toulouse for an estimated £9.94m.
The Danish international arrived with a reputation for pace, hoping to provide a cutting edge to Boro’s attack following their relegation from the Premier League.
Despite flashes of promise, his time at the Riverside was relatively short-lived. He struggled for goals and later moved on, but his transfer still marks him as one of the club’s most significant investments in recent years.
4. Jordan Rhodes
In the 2015/16 season, Middlesbrough added to their attacking options by signing centre-forward Jordan Rhodes from Blackburn for an estimated £8.81m.
Rhodes arrived with a notable goalscoring record in the Championship and was expected to fire Boro back into the Premier League.
While he did play a part in the club’s promotion that season, his impact on the scoresheet was not as dominant as many had hoped, given his beefy price tag.
His time at the club was relatively short, yet his transfer remains one of the largest in Middlesbrough’s history.
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3. Ugo Ehiogu
A cornerstone of Middlesbrough’s defence, Ugo Ehiogu arrived as a centre-back in the 2000/01 season from Aston Villa for an estimated £7.56m.
Ehiogu became a fan favourite at the Riverside, forming a partnership with now former England manager Gareth Southgate.
He was integral to the most successful period in the club’s history, notably helping Boro lift the League Cup in 2004 – their first major trophy.
His imposing presence and consistent performances solidified his status as a club legend, making him a truly worthwhile investment for over five seasons.
2. Afonso Alves
Middlesbrough broke their transfer record in the 2007/08 season to bring centre-forward Afonso Alves from Heerenveen for an estimated £11.56m.
The Brazilian arrived with an incredible goalscoring reputation from the Eredivisie, and his signing generated immense excitement among the Boro fans.
While he did score some memorable goals, including a hat-trick against Manchester City, he struggled to consistently replicate his prolific form in the Premier League.
His high-profile move remains a significant, yet ultimately mixed, chapter in Middlesbrough’s transfer history.
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1. Britt Assombalonga
Britt Assombalonga became Middlesbrough’s most expensive signing in the 2017/18 season, joining as a centre-forward from Nottingham Forest for an estimated £15.05m.
He was brought in to spearhead Boro’s attack and provide the goals needed for a return to the Premier League.
Assombalonga quickly proved himself as a key player, becoming the club’s leading scorer in several seasons during his tenure.
His pace, power, and clinical finishing made him a constant threat and a firm favourite among supporters, delivering consistent goalscoring returns over four seasons at the Riverside.