Middlesbrough FC massively hit the jackpot with £4.5m star and these 5 others | OneFootball

FLW takes a look at six times Boro hit the transfer jackpot from the summer of 2004 onwards...

Middlesbrough have seen some quality players arrive at the Riverside Stadium over the last two decades, with some top talent donning the red and white shirt both in the Championship, and the Premier League.

Boro are looking to reclaim their place in the top-flight this season, with head coach Michael Carrick boasting a talent-laden squad that appears to hold real promotion claims.

Middlesbrough's recruitment has made a notable improvement since the arrival of head of football Kieran Scott in 2021, with shrewd signings, bargain buys and major profits made on numerous additions.

Over the last 20 years, the Teessiders have reached the heights of a UEFA Cup final, to the lows of narrowly avoiding relegation to League One, as well as a couple of play-off heartbreaks and unforgettable moments along the way.

During that time, the club have made some fantastic signings, which have produced cult heroes, club legends, provided the stage for some superb careers on Teesside, and some major returns on their investments.

FLW takes a look at six times Middlesbrough hit the transfer jackpot from the summer of 2004 onwards. This list is in no particular order.

George Friend

Certain players just get what it means to wear a certain club's badge on their chest, and that's certainly the case with George Friend and Middlesbrough.

"Gorgeous" George was signed for just £100k from Doncaster Rovers in the summer of 2012, and over the next eight years, would forge a legacy that will see him forever hold a place in the hearts of Teessiders everywhere.

Friend was a stalwart at the left-back position for Middlesbrough, and played a vital role in helping the club build towards eventual Premier League promotion in 2016.

He was a leader on the pitch and in the dressing room, pouring every ounce of blood, sweat and tears he could into every minute he wore the Boro shirt. As a result, he developed a bond with Middlesbrough supporters to a level that had rarely been seen before, or indeed since.

A fantastic player, a wonderful ambassador for the club and the Teesside community, and undoubtedly one of the biggest bargains in the club's recent history.

Jimmy Floyd Hasselbaink

Having signed for Chelsea in 2000 for a fee £15m, which made him the joint most expensive signing in British football history at the time, Middlesbrough signed Jimmy Floyd Hasselbaink on a free transfer following the expiration of his contract at Stamford Bridge just four years later.

Despite being 32 at the time of his Boro switch, the legendary striker still had plenty of gas left in the tank, and he would waste no time putting his foot to the floor on the way to becoming a Riverside icon.

13 goals in 36 Premier League appearances during his debut 2004/05 season saw him shoot to an instant fan favourite in the North East, before following that campaign up with nine goals in 22 top-flight outings in the 2005/06 season.

A centre-forward that just oozed class, Hasselbaink scored some truly memorable goals during his two years with Middlesbrough. Vital strikes in Europe, a bullet of a free-kick against Manchester City, and superb strike in a Wear-Tees Derby clash with Sunderland at the Stadium of Light.

Grant Leadbitter

One of the finest Middlesbrough captains in modern times, and all for the price of absolutely nothing. Grant Leadbitter's free transfer from Ipswich to Boro in 2012 was the start of a wonderful six-and-a-half year career on Teesside.

A Sunderland fan by birth and a former Black Cats player, surely he would have no chance of winning the hearts of the Riverside faithful? Well, like that old saying goes: 'Play for the name on the front, and they'll remember the name on the back'.

Few have done that better in a Middlesbrough shirt than Leadbitter did during his time with the club, as he lead Boro away from the dark and unsettled times of the recent Gordon Strachan era, and skippered the side towards a brighter future that would lead to the Premier League.

His 2014/15 season was one of the most impressive individual campaigns from a Middlesbrough central midfielder in a long time, scoring 11 goals and providing nine assists in 46 Championship appearances.

Leadbitter's role may have faded after Boro's promotion to the Premier League and their subsequent relegation, but after arriving at a time when the club sorely needed an injection of passion and pride from those wearing the shirt, he played a huge part in recapturing the imagination of the fanbase.

Mark Viduka

Signed for just £4.5m from Leeds United in the summer of 2004, Mark Viduka's three years on Teesside would ensure he'd be heralded as one of Middlesbrough's greatest centre-forwards of the modern era.

Power, strength, superb technical ability, a cannon of a strike and a real threat in the air; the Australian had everything you'd want from a striker designed to spearhead your attack.

Viduka played a pivotal role during Middlesbrough's two UEFA Cup campaigns, and scored some vital and iconic goals on the way to the final in 2005/06.

He was prolific in the Premier League too, with his final season being his best scoring campaign in a Boro shirt. Viduka bagged 14 goals in 29 top-flight appearances in the 2007/08 season, before departing for Newcastle United in the summer of 2007.

Morgan Rogers

Morgan Rogers may not have enjoyed the glittering Middlesbrough career like the other names on this list, but when talking about hitting the jackpot, Boro won the lottery with his signing in the summer of 2023.

Signed for a mere £1m, Rogers presented as a signing that would require patience, having yet to prove himself at Championship level at that stage of his career.

However, in the space of just six months, Carrick had helped turn Rogers into a player that Aston Villa were more than happy to hand over up to £16m for, bringing in profits that will continue to help fund transfers for multiple windows to come.

Since leaving the Riverside, Rogers has gone on to establish himself as one of the finest young talents in the Premier League, and has earned multiple England caps too.

Emanuel Pogatetz

Middlesbrough have had some great defenders in their time, but few have been as brilliantly barmy as Emanuel Pogatetz.

"Mad Dog", as he became known at the Riverside, signed for just £1.8m from Bayer Leverkusen in the summer of 2005, and over the next five years, his combative and passion-fuelled approach to defending saw him become adored by the Boro support.

Pogatetz was booked 23 times in all competitions across his first two seasons at the Riverside, and will no doubt have had opposition strikers quaking in their boots at the prospect of having to go up against the Austrian.

Former Middlesbrough manager Steve McClaren was once quoted describing Pogatetz as someone who "never, ever, gives less than 300 per cent in performances", but what can get lost in the character that he was is just how good of a defender he was.

He made 158 appearances for the Teessiders between 2005-10, before departing for Bundesliga side Hannover 96 in the summer of 2010. Pogatetz is still fondly remembered at the Riverside today thanks to the warrior that he was in a Middlesbrough shirt, and his excellent performances.