Ronaldo, Rooney, Cole: The biggest deadline-day transfers

Check out these transfer deadline-day deals that sent shockwaves through football history

Last updated:
Robert Ilsley, Sports Reporter
The transfer deadline-day can offer some huge surprises
The transfer deadline-day can offer some huge surprises

Dubai: With just one day to go until the summer transfer window closes, club officials will be scrambling to get their final deals over the line.

From record-breaking moves to last-minute surprises, here are some of the biggest deadline-day deals in football history.

Cristiano Ronaldo to Man United

There can be no other place to start then Ronaldo’s return to Manchester United in 2021.

With the Portuguese superstar seemingly on his way to rivals Manchester City from Juventus, United moved quickly to hijack the transfer and bring their former hero back to Old Trafford.

The deal was completed on August 31, with Ronaldo returning to the club where he had first established himself as a global superstar.

Mesut Ozil to Arsenal

The German’s move from Real Madrid to Arsenal in 2013 was one of the most memorable deadline-day deals of all time.

Arsenal stunned the football world by agreeing a deal worth around £42.5 million for the German playmaker, smashing the club’s transfer record in the process. The excitement was palpable around the Emirates, with hundreds of Arsenal fans gathering outside the stadium and going wild as news of the deal emerged

After years of frustration over the club’s spending, Ozil’s arrival felt like a statement of intent, and one of the most unexpected deadline-day coups in Premier League history.

Wayne Rooney to Man United

United paid almost £30 million for the then 18-year-old, making Rooney the most expensive teenager in football history when the deal was done in 2004.

The transfer was also hugely controversial given Rooney’s roots in Liverpool and the fierce rivalry between Everton and Manchester United’s northern rivals, Liverpool.

For an Everton-born Scouser who had emerged from the city’s footballing culture, moving to one of England’s biggest clubs made the deal all the more explosive.

Robinho to Man City

The Brazilian’s move from Real Madrid to Manchester City in 2008 was one of the biggest deadline-day shocks the Premier League has ever seen.

The Brazilian had been heavily linked with Chelsea throughout the summer and, such was the late nature of City’s intervention, reports suggested Robinho himself believed he was heading to Stamford Bridge.

Instead, City pulled off a remarkable hijack and completed the deal on deadline day, with Robinho reportedly only realising he was joining Manchester City rather than Chelsea once the transfer was effectively done. It was a stunning statement of intent from City, coming just days after the club’s takeover by the Abu Dhabi United Group.

Ashley Cole to Chelsea

In a move which still makes many Arsenal fans hate him to this day, Cole swapped north London for Chelsea on deadline day in 2006.

The left-back had been a key part of Arsenal’s famous Invincibles side, making his decision to join one of the club’s biggest rivals particularly difficult for supporters to accept. The deal, which also saw William Gallas move to Arsenal, was widely viewed as a case of money coming before loyalty, with many Arsenal fans believing Cole had turned his back on the club for a more lucrative contract at Chelsea.

The bitterness surrounding the transfer ensured Cole’s name became synonymous with one of the most controversial Premier League deadline-day moves.

Robert Ilsley
Robert IlsleySports Reporter
Rob is an experienced sports reporter with a focus on digital publishing. He holds both an undergraduate and master’s degree in sports journalism and has hands-on experience in presenting and commentary. Rob has previously worked in the communications teams at Premier League clubs Everton and Brentford FC. While football is his main passion, he enjoys all sports and loves sharing his enthusiasm with anyone he meets.

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