Rivaldo, Ronaldinho and Diego Forlan were all linked with moves to Middlesbrough.
Before Middlesbrough brought in Victor Valdes, Aitor Karanka made a move for Gent goalkeeper Matz Sels. The Belgian stopper drew plenty of Premier League suitors but would end up opting for a move to Championship side Newcastle United. Sels told the Sunderland Echo that he chose the Magpies because they are “a really big club”.
Victor Lindelof has been linked with a £20.5million move to Manchester United this window, but the Benfica man could have been Middlesbrough’s for just a fraction of that price. According to the Gazette Live, Boro had agreed a deal in principle to bring in the Swedish centre-back last January for just £3million. However, an injury to Lisandro Lopez saw Lindelof thrust into the first-team and soon derailed his move to the Riverside. Any hope of reviving the transfer was quickly gone when the youngster’s performances began to turn the heads of United, Juventus, Barcelona and Bayern Munich.
In 2009, Middlesbrough boss Gareth Southgate was seeking a replacement for centre-back Robert Huth. Southgate decided on a move for Celtic veteran Bobo Balde, who had six months remaining on his contract. As reported by Sky Sports, Balde would reject Boro’s offer and see out the rest of the season at Parkhead.
Sylvain Distin looked set for Teesside when Middlesbrough agreed an undisclosed deal with Manchester City to bring in the Frenchman. The Telegraph reported that Distin was in talks with the club about a summer move in 2006, as Boro searched for Gareth Southgate’s replacement. However, the transfer would stall when the club failed to agree personal terms with Distin, according to the Standard.

Liverpool star Adam Lallana recently admitted that he could have signed for Middlesbrough back in 2010. The England international told to the Scottish Sun that Gordon Strachan was interested in bringing him in when Southampton were struggling for money.
Nemanja Matic has also revealed that he came close to signing for Middlesbrough. The Chelsea midfielder had a trial at the club in 2009 when he was still playing for MFK Kosice. Matic told the Mirror: “I don’t know why it didn’t happen – I went to join up with the national team and the clubs were supposed to talk, but I never heard any more about it.” Chelsea would end up securing the Serbian’s signature shortly after.
In 2003, Steve McClaren made an audacious bid to bring World Cup winner Rivaldo to the Riverside. The Gazette Live reported that Boro’s hierarchy were trying to put together a wage package for the Brazilian, who had just been released by AC Milan, and were “much closer” to making a deal happen. Rivaldo would eventually agree a deal with Greek club Olympiacos.
Four years later, an ambitious move was also on the cards for Rivaldo’s international teammate Ronaldinho. The Telegraph reported that Boro offered Barcelona £10million for the two-time World Player of the Year winner. Unfortunately, a deal to bring Ronaldinho to Middlesbrough never materialised, and the legendary footballer would end up signing for AC Milan in 2008.
As Steve McClaren began to lose faith in his goal-shy strikers, the Boro boss turned to midfielder George Boateng for advice on which Dutchman to bring to the Riverside: Patrick Kluivert or Jimmy Floyd Hasselbaink. As written in Dave Allan’s book ‘A Small Town in Europe’, Boateng told McClaren that “if he wanted to achieve something and have real go at European football with a leader who would fight and scrap for everything as well as score goals then I would say go for Jimmy.” The Boro boss took that advice and signed Hasselbaink instead of Kluivert, who would head to local rivals Newcastle.
Middlesbrough came agonisingly close to securing the signature of Diego Forlan, only for Manchester United to swoop in at the last moment. Boro chief executive Keith Lamb told Sky Sports that, with transfer fee and personal terms agreed, Forlan was about to catch a flight to England when he received an 11th-hour approach from Manchester United. The Uruguayan decision was made when he took a flight to Manchester rather than Newcastle, before signing on the dotted line for Sir Alex Ferguson’s side.
Earlier this month, Olivier Giroud’s ‘scorpion’ goal was the envy of every Premier League side, but the Frenchman could have been a Middlesbrough player had a deal gone through in 2009. Giroud confirmed to the Express that there was interest in him from Boro while he was playing for French side Tours.
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