Football League World
·19 luglio 2025
Why Middlesbrough & Sunderland supporters share affection for versatile midfielder despite crossing Tees-Wear divide

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·19 luglio 2025
Discover the incredible journey of Dean Whitehead, the midfielder who won promotions with both Sunderland and Middlesbrough.
Dean Whitehead was a promotion winner with Sunderland, but wrote his name into the history books at rivals Middlesbrough too.
The midfielder made close to 200 appearances for the Black Cats, and more than 60 for Boro, with both sets of fans both sharing affection for him despite the fact that he planted his feet in both camps during his playing career.
At Sunderland, he was part of two promotion-winning teams after joining from Oxford United, where he came through the youth ranks.
Whitehead was one of the club's top performers as Mick McCarthy led the side to the Premier League by the end of the 2004/05 season. Usually operating in the centre of the park, he was pulled into wide areas when the squad required it, showing his adaptability and willingness to get stuck in however he was needed.
As a utility player, the Englishman stood out and was often praised by fans and teammates alike, with him winning the Players' Player of the Year accolade as Sunderland returned to the top-flight.
When Sunderland were soundly dumped back into the EFL the following season, he was one of very few bright spots in the team. This time picking up the Player of the Year award, Whitehead wore his heart on his sleeve and showcased a desire that fans of any stripe love.
He was listed in the 2006/07 PFA Team of the Season for the Championship after helping the Black Cats bounce back from relegation to win the second-tier crown. There was no doubting his status as a legend at the club, with two promotions and no shortage of personal accolades under his belt by the time he swapped Sunderland for Stoke City in 2009.
He was a consistent force, playing no less than 28 games per season during his spell at the Black Cats, and being named captain under manager Roy Keane.
Whitehead helped push the club away from relegation in his final season at the Stadium of Light, marking his name as a key part of what can be recalled as a successful time for the club despite some turbulent ups and downs.
He eventually signed for Boro on a free transfer in the summer of 2013, before going on to spend two years on Teesside.
Stoke City was his landing spot after leaving Sunderland, with a £3m deal agreed in 2009. He reached an FA Cup final and Europa League quarter-final with the Potters, before heading back to the North East.
He went on to captain the Middlesbrough side on numerous occasions during his stint at the Riverside Stadium, and provided an invaluable quality in terms of his versatility, which was first on display at Sunderland.
He covered both in midfield and across the defensive line, plugging gaps wherever he was needed in a way that provided no end of depth to the Middlesbrough outfit.
While his part in two promotions into the Premier League ensures he is remembered fondly by the Black Cats, it was an appearance in a shock FA Cup tie that puts his name in the Boro history books.
He played the full 90 minutes as the side pulled off a memorable shock at the Etihad Stadium, beating a star-studded Manchester City by two goals to nil on their own patch.
The attacking edge he had at Sunderland, being deployed in areas further up the field or out wide, was lost when he moved to Middlesbrough. Whitehead scored just once in 63 appearances for the club, but he became known as a reliable, adaptable, and trusted figure on the other side of the Tees-Wear derby.
He eventually moved to Huddersfield Town after Boro lost a play-off final to Norwich City. There he again won promotion into the Premier League, before calling time on a successful playing career and taking up a coaching in West Yorkshire.
It brought to an end his association with the Tees-Wear derby, but not before he managed to become a familiar and loved player for both Sunderland and Boro. As a part of two promotion-winning teams and a starter in one of Middlesbrough's great FA Cup showings, Whitehead has a great legacy in the North East.