Take a look at the most expensive transfer signings of all time in Middlesbrough history, brought to you by Boro News.
Despite languishing in the Championship for several years now, Middlesbrough have been a regular feature in the Premier League throughout its history, with chairman Steve Gibson always willing to put up the cash to help his club.
However, Boro have a varied record when it comes to spending big money throughout the club’s history, with a number of their record signings going to be rather large flops.
There have been a few smart investments made by the Teessiders, but it is certainly a mixed bag.
With this in mind, here is a look at Middlesbrough’s ten most expensive transfer signings of all time – as per Transfermarkt.
10 – Jonathan Woodgate – £8.12m
After an ill-fated spell with Real Madrid, which included an own goal and red card on his debut, Jonathan Woodgate joined Middlesbrough on loan in 2006 before making a permanent move to Teesside in 2007.
Woodgate made 112 appearances for Boro across his three stints at the club, leaving for Tottenham in 2008 before returning on a free transfer in 2012 to end his career in his hometown.
9 – Gareth Southgate – £8.24m
The early 2000s saw Middlesbrough willing to spend big as Steve Gibson aimed to take the North East outfit to the next level. No player better sums up this period than Gareth Southgate.
The now-England manager linked up with the Teessiders from Aston Villa in 2001 and went on to cement himself as one of the club’s greatest-ever players.
He made 204 appearances for Boro and captained them during their most successful period, which included a 2004 League Cup final triumph and a UEFA Cup (Europa League) final defeat to Sevilla in 2006, which proved to be Southgate’s last game as a player.
8 – Yakubu Aiyegbeni – £8.24m
Looking to capitalise on their League Cup success and the European football it brought with it, Boro signed Yakubu from Portsmouth in 2005.
He spent just two seasons at the Riverside before joining Everton in 2007 but remains one of Middlesbrough’s most successful strikers of the Premier League era, netting 35 and assisting 11 in 104 appearances.
7 – Fabrizio Ravanelli – £8.27m
Short but sweet is perhaps the best way to describe Fabrizio Ravanelli’s time on Teesside. The Italian scored a staggering 31 goals and provided 10 assists in 47 appearances after moving from Juventus ahead of the 1996/97 campaign.
Middlesbrough reached the League Cup and FA Cup finals that season, losing out to Leicester and Chelsea in both showpieces.
Despite their cup success, Boro were relegated from the top flight at the end of 96/97, with Ravanelli moving to Marseille that summer.
6 – Marten de Roon – £8.88m
After securing promotion to the Premier League in 2015/16, Middlesbrough spent big under Aitor Karanka as they aimed to avoid the drop.
Among the names brought in was promising midfielder, Marten de Roon.
The Dutchman made 36 appearances for Boro and scored five goals but he was hampered by the club’s struggles both on and off the pitch as they were swiftly relegated back to the Championship.
De Roon returned to Atalanta just one year after leaving for Boro and has shown his true quality for club and country since that move.
5 – Martin Braithwaite – £9.56m
After their most recent relegation from the Premier League, Steve Gibson was quick to take advantage of the generous parachute payments available to the club, spending close to £50m on players in the 2017 summer transfer window in a bid to secure a swift return to the top-flight.
Martin Braithwaite was one of the stars brought in that summer, signing from French outfit Toulouse.
However, things did not work out for the Dane as he made just 40 appearances and scored nine goals for Boro. He was loaned out several times before being sold to CD Leganes in 2019.
4 – Jordan Rhodes – £10.07m
Jordan Rhodes’ transfer from Blackburn Rovers to Middlesbrough midway through the 2015/16 campaign may be viewed by some as a waste of money.
He made just 24 appearances for the Reds and scored six goals before being sold to Sheffield Wednesday in 2017.
However, those six goals were crucial to Boro securing promotion to the Premier League in 2015/16, with the striker earning Aitor Karanka’s side seven points via his efforts.
3 – Ugo Ehiogu – £10.32m
Ugo Ehiogu joined Middlesbrough in 2000, leaving Aston Villa to rekindle his infamous defensive partnership with Gareth Southgate at the Riverside.
The centre-back played 151 games for Boro and, like Southgate, was a key cog in the club’s success midway through the 2000s.
Ugo Ehiogu left Middlesbrough for Leeds in 2006.
2 – Afonso Alves – £14.38m
Few Middlesbrough fans will argue that Afonso Alves is the biggest flop in the club’s history.
The Brazilian linked up with the Teessiders in 2008 after scoring 48 goals in 50 outings for Eredivisie side, SC Heerenveen
That form vanished at the Riverside, however, with Alves finding the net just 13 times in 49 games before being sold to Al-Sadd SC just 18 months after becoming Boro’s record signing.
1 – Britt Assombalonga – £14.46m
Alves’ stint as Middlesbrough’s record signing was finally ended in 2017 when Britt Assombalonga was signed from Nottingham Forest as Steve Gibson looked to back Gary Monk to return his club to the Premier League.
The striker’s time in the North East was by no means terrible, scoring 47 in 161 appearances, but he struggled to repeat the form he had shown at Nottingham Forest in previous seasons.
Assombalonga left Middlesbrough for Turkish outfit Adana Demirspor on a free transfer in 2021.