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Premier League 25th Anniversary: Top 25 Transfers

As the Premier League reaches its 25th year, RealSport looks at 25 of the transfers that made it arguably the most exciting league in the world.

Since its inception, the Premier League has grown and developed into one of the most thrilling football leagues in the world, followed by millions of people from every continent. 

The league has also established itself as a top destination for professional footballers seeking a genuine challenge. As a result, we’ve seen some of the world’s best players ply their trade here. There have also been players who have come in and created absorbing narratives all on their own.

In no particular order, we highlight transfers that we think have made the Premier League what it is today.

1. Gianfranco Zola [Parma to Chelsea, £4.5m]


In the history of the Premier League, few players have had the rare distinction of also being liked and respected by their rival fans. Gianfranco Zola arrived when club manager Ruud Gullit was trying to bring a more continental style to the team and English football.

Zola was a diminutive genius whose tricks, flicks and ability to find space spoke to a higher level of understanding of football. 59 goals and 42 assists in 229 league appearances were enough for Chelsea fans to vote him in as their best player ever.

2. Thierry Henry [Juventus to Arsenal, £11m]


Not too many fans were bothered about Thierry Henry’s arrival at Arsenal. However, after 175 goals in 258 appearances, 4 Golden Boot awards and 2 Player of the Year prizes won, Henry left the Premier League widely acknowledged as one of its greatest players.

In his prime, he was one of the closest things to a complete striker if there ever was one. Moving with a grace that belied his 6’2 frame, Henry would combine his pace and trickery to bamboozle defenders. His goal record also points at expert finishing. He would go on to become Arsenal’s record goalscorer.

3. Eric Cantona [Leeds to Man United, £1.2m]


Despite playing under the iron-fisted rule of Alex Ferguson, Eric Cantona was afforded a wide berth. He rewarded this trust with goals that steered Manchester United to their first title in 26 years. He was a controversial figure in the Premier League, but his magical madness was what made him so enthralling to watch.

With a puffed-out chest and the upturned collar, Eric Cantona walked around with an unabashed swagger. Bringing a winning mentality to Manchester United, the famed Class of ’92 would learn from the confident Frenchman as they went on to dominate the league in a defining era.

4. Sami Hyypia [Willem II to Liverpool, £2.6m]


When he first arrived, Sami Hyypia was not expected to make the grade at Liverpool. He defied his doubters by becoming a key component in Liverpool’s resurgence as a title contender in the early-to-mid 2000s. 

His dependable partnership with Stephane Henchoz provided the defensive base for the tactical football the team was known for. Such was Hyypia’s assuredness that despite the frenetic pace of the Premier League, Hyypia only garnered one red card, the only one in his professional club career.

5. Claude Makelele [Real Madrid to Chelsea, £16.8m]


When Real Madrid sold Claude Makelele to Chelsea, it was a great boost for the Premier League. In the fast-paced style of the English game, Makelele bossed the midfield for the London side and revolutionised the defensive midfield position.

Makelele brought a refined athleticism to the role. He showed how reading the game, timing challenges could be far more useful than having a regular bruiser. His ability to pass intelligently also caught the eye of those who followed the league. Before Makelele, there was an under-appreciation for what defensive midfielders like him could do. His time in the Premier League definitely changed more than a few minds.

6. Sergio Aguero [Atletico Madrid to Man City, £38m]


Every great team needs a great striker. In Manchester City’s recent history, none have been as deadly and consistent as Sergio Aguero. With 122 goals from 181 appearances, Aguero’s stellar strike rate has been a leading factor in City’s two title triumphs.

Aguero has all the hallmarks of a great Premier League striker. He is quick, clever and is a natural finisher, which gives him a great advantage in converting all the chances that come his way. It is telling that although he has had to deal with a few injuries, he has remained effective whenever he has played.

7. Dennis Bergkamp [Inter to Arsenal, £7.5m]


Arriving just a year before Arsene Wenger, Dennis Bergkamp was the perfect orchestrator for the new brand of football that the manager wanted to introduce. 

An astute passer of the ball, the Dutchman was one of those players who always seemed to have time and space on the ball. He operated in an advanced midfield position which was often crowded, but he would dance through effortlessly. He seemed to exert maximum grace with minimum effort, unbothered while making the perfect pass or shot. It’s no wonder he was nicknamed ‘The Iceman’.

8. Paolo Di Canio [Sheff Wed to West Ham, £1.5m]


As far as controversial figures go, Paolo Di Canio is right up there with the best of them. He was already serving an 11-match ban for shoving referee Paul Alcock while at Sheffield Wednesday before taking his talents to West Ham.

While at West Ham, he cemented his reputation as a fiery, but supremely talented footballer. On the back of his efforts, West Ham finished in a league high 5th position and qualified for Europe.

Whenever he played, fans never knew if he would get sent off or do something unexpectedly magical with the ball. He was a divisive character, but he was one that definitely livened up the Premier League.

9. Frank Lampard [West Ham to Chelsea, £11m]


Roman Abramovich’s era saw a parade of star names call Stamford Bridge their new home, but it was a previous transfer that proved to be one of their most fruitful ones. In 13 years at Chelsea, Frank Lampard went from a young midfielder brimming with potential to becoming one of the best the Premier League had ever seen.

Lampard was not the most technical midfielder or the most skilled. Yet, from an advanced midfield position, Lampard posed a direct goal-scoring threat at a level few midfielders could hope to achieve.

His ability to shoot from outside the box helped him yield 147 goals from 429 league appearances. These goals were crucial to Chelsea’s success and the West Ham graduate became a firm favourite in the hearts of Chelsea supporters everywhere. 

10. Xabi Alonso [R. Sociedad to Liverpool, £10.7m]


Before he became a European legend, Xabi Alonso continued building his reputation with a move to the red half of Merseyside. Alonso was an elegant passer, the antithesis to the kick and rush style that dominated the early years of the Premier League. 

Although he was more measured, he was not docile. His accurate passing helped Liverpool to launch quick counter-attacks, leaving the opposition struggling to catch up.

His reading of the game also showed how a defensive midfielder could play his part with no need to be a bruiser. Alonso brought a touch of continental class that the Premier League audience could appreciate. 

11. Tim Cahill [Millwall to Everton, £1.5m]


After leaving an established career with Millwall, Australian Tim Cahill made the step up to Premier League football and never looked out of place. His prowess as an attacking midfielder even helped Everton break the monopoly of the top four clubs.

Tim Cahill’s ability to time his runs in the box meant that he could score an astonishingly disproportionate amount of headed goals for someone of his build. He characterised Everton’s desire to continually and successfully punch above their weight. With Cahill in their team, Everton were difficult opponents for any team in the league.

12. Robbie Keane [Leeds to Tottenham, £7m]


Despite joining Tottenham at the age of 22, Robbie Keane had already played for four different clubs. It was in his first spell (of three!) at Tottenham that we saw Robbie Keane at his best. In each of his first six seasons, he scored over 10 league goals every season.

Before his move to Liverpool, Keane was considered to be one of the best strikers outside the top four. He was quick, clever, lethal and had the ability to play with a number of different strike partners. Spurs’ commitment to attacking football suited Keane and he was able to thrive as an entertaining player to watch in the Premier League.

13. Luis Suarez [Ajax to Liverpool, £22.8m]


Despite an inglorious end to his Liverpool career, Luis Suarez was one of the most exhilarating players to feature in the Premier League. His arrival gave Liverpool’s attack a dynamic style, the blueprint for which they are still following today.

Suarez had the skill and trickery required of a speedy forward but he also had an air of unpredictability and doggedness about him. It did not matter how the opposition tried to restrict him. Suarez believed he could find another way. His presence distracted defenders and gave his fellow attackers much more space to exploit. With Suarez, Liverpool were the closest to winning the elusive title.

14. Alan Shearer [Blackburn to Newcastle, £15m]


Alan Shearer may have won the Premier League title with Blackburn, but it was his transfer to hometown club Newcastle United that helped him become a Premier League legend. In today’s world of false nines and wide forwards, Shearer was a throwback to the old-school English centre-forward.

With 148 goals in 303 games, Shearer was a model of consistency. No matter the circumstances surrounding his club, Shearer could be counted on to find the back of the net.

Give him the ball in the box and he would score. No fuss. With the majority of his goals at Newcastle, Shearer remains the top goalscorer in Premier League history.

15. Jay-Jay Okocha [PSG to Bolton, free]


Under Sam Allardyce, Bolton Wanderers gained a reputation for route-one style football and the term ‘winning the second ball’ gained mainstream popularity. Almost paradoxically, the Bolton manager also brought in several veteran players who were more technically adept. Perhaps it was an awkward attempt to balance the team out. One of these players was Jay-Jay Okocha.

The wonderful thing about Okocha is that whenever he played, it felt like he was playing a game of football with his friends in the street, instead of a high-stakes professional game in England’s top divisions.

Fans of both teams always waited to see Okocha show off his unique brand of tricks, flicks and mastery of the ball whenever Bolton played.

16. Clint Dempsey [New England to Fulham, £4m]


Although the most Fulham achieved during Clint Dempsey’s time was a 7th place league finish that led to a barnstorming run in the Europa League, he was definitely a great buy for Fulham. Dempsey’s arrival and eventual success showed how American outfield players could succeed in the Premier League.

Combining the athleticism expected of American footballers with advanced technical ability, Dempsey was a tall, rangy player who could find his out of tight situations and score. Manager Roy Hodgson made his Fulham side difficult opponents, and it was Dempsey the American, who was the star man.

17. David Ginola [Newcastle to Tottenham, £2.5m]


David Ginola was an extravagant player with an extravagant personality. After falling out of favour with Kenny Dalglish, Ginola moved to North London and in Tottenham, joined a club that fit with him.

Ginola was a skilled dribbler who would mesmerise the crowd with his weaving runs. Ginola wore his French panache like a badge of honour. If he played, it had to be with style.

His skill and creativity were acknowledged when he became the first player playing for a club outside the top four to win PFA Player of the Year and FWA Footballer of the Year awards. 

18. Patrick Vieira [Milan to Arsenal, £3.5m]


As Arsenal sashayed their way to the top with their unique brand of attacking football, they needed an enforcer who could also play. Not only did Patrick Vieira shoulder the responsibility, he became the beacon of inspiration for a talented and powerful Arsenal side.

Arsene Wenger’s best teams had the ability to combine free-flowing football with a steely approach and Patrick Vieira was the best embodiment of those qualities.

With him as the midfield engine, Arsenal could push aside all comers in their season of ‘Invincibles’. Vieira played fearlessly and his influence permeated throughout the team.

19. Petr Cech [Rennes to Chelsea, £7m]


Soon after Petr Cech arrived at Chelsea, he stepped in for the incumbent Carlo Cudicini, after the latter suffered an injury in pre-season. Since then, Cech has not looked back.

He had great reflexes, positioning and command of his area. Although he was young, Cech immediately showed that he was up for being the number one at a club now seriously pushing for the title.

Cech made good on that potential, winning the Golden Glove award three times as he played his part in Chelsea’s four title wins. His world class performances in the Premier League have established him as a respected, world-class goalkeeper.

20. Luka Modric [D. Zagreb to Tottenham, £16.5m]


There were doubts that a player with Luka Modric’s slight build could survive the bruising central midfield encounters in the Premier League. Modric would not only prove his doubters wrong, he would smash those doubts to smithereens.

Modric was a central midfielder who operated primarily as an attacking force. Good with both feet, he established dominance in a game by whizzing around his opponents, picking out his fellow attackers.

Crucially, Modric is also good at keeping the ball under pressure, a quality that flummoxed many opponents as he left them twisted. With the right application of skill and technical ability, Modric was a prime example of how the best players could succeed anywhere. 

21. Vincent Kompany [Hamburg to Man City, undisclosed]


In their meteoric rise to the top, Manchester City needed a steady hand to the steady the ship. As City’s expectations and performances grew better, so did Vincent Kompany. City had a plethora of individual stars but to win the title, they needed to play as a team.

Kompany provided a stabilising influence that the team needed. Knowing they could rely on Kompany to protect them at the back gave Manchester City the confidence to go out and attack the opposition. It paid off as City finally won their first ever Premier League title, with Vincent Kompany as captain.

22. N’Golo Kante [Caen to Leicester, £5.6m]


Two Premier League titles in his first two Premier League seasons with two different clubs make N’Golo Kante a very efficient winner. Coming from unheralded Caen, Kante played a major part in Leicester’s run to the title. Kante was an unlikely player who drove his team on to become the unlikeliest of champions.

His indefatigable style was a sight to behold. Despite a slight frame, Kante was a deceptively strong player who was a pest for his opponents. He was quick and intelligent, which gave him the ability to be everywhere at once. He was so good that that fans and media alike dubbed him the rightful heir to the ‘Makelele role’.

23. Sol Campbell [Tottenham to Arsenal, free]


We almost didn’t include this one because of the controversy and the sheer audacity. Sol Campbell was expected to move to Europe for Champions League football but instead, he chose to join their arch-rivals Arsenal. 

Campbell was a man-mountain who was able to move quickly to close down opponents. For all their attacking power, Arsenal might not have gone a whole season undefeated without Campbell in their ranks.

Campbell’s move added even more tension to the rivalry between Arsenal and Spurs. But if you were a neutral fan, it just made good drama for the league.

24. Cristiano Ronaldo [Sporting to Man United, £12.24m]


The number seven jersey is somewhat revered at Old Trafford. Expectations were high when Manchester United bought Cristiano Ronaldo and assigned him the vaunted jersey number. However, his talent was painfully apparent. He had stepovers for days and wanted to take on everybody in his path with youthful abandon. Murmurs of excitement floated from the stands every time he got the ball.

But it was his evolution from one trick pony to attacking powerhouse that makes his story interesting. Playing for a team seeking to regain glory, Ronaldo honed his craft, cut out the unnecessary and learned to become one of the world’s finest attackers. All the while, the Premier League audience had a front row seat to his fascinating development.

25. Didier Drogba [Marseille to Chelsea, £24m]


If there was a player that represented Chelsea manager Jose Mourinho’s take-no-prisoners attitude on the field, it had to be his star striker, Didier Drogba. The Ivorian was a no-nonsense, imperious target man whose purpose was to bully his opponents into submission by scoring lots of goals.

He did just that, scoring 100 league goals for Chelsea. Many Premier League defenders dreaded playing Drogba. It was almost impossible to bully him off the ball and he rapidly came alive whenever the ball was in the box. He was such an interesting problem for Premier League defences because he was equal parts brutal, swift and deadly.

We’re aware that we’ve probably missed out on some absolute gems in crafting this limited list. If you’ve got a transfer that you think should have really been included, let us know in the comments below!

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Khairul Annuar

A Manchester United fan since 1994 thanks to the enigmatic and controversial Eric Cantona, Khairul also follows a number of other sports. His bucket list includes visits to the many famous sporting arenas around the world.

Premier League 25th Anniversary: Top 25 Transfers

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