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July 1 2009 was the day that Manchester United supporters had their hearts broken as their hero Cristiano Ronaldo made his dream move to Real Madrid.

Following six glorious seasons with the Red Devils – in which Ronaldo scored 118 goals in 292 games and won three Premier Leagues, a Champions League and an FA Cup – the now 36-year-old was given permission to fulfil a life-long goal and join Los Blancos for a then world record transfer fee of £80m.

The rest, as they say, is history, with Ronaldo going on to smash record after record in the Spanish capital and win everything possible during a stunning nine year spell at the Bernabeu.

What is not remembered quite so well, however, is who United ended up bringing in that summer once they got over the disappointment of Ronaldo's departure.

Here is a look back at the four players who made the move to Old Trafford that summer and how they fared…

1. Antonio Valencia (signed 30 June)

Antonio Valencia was undoubtedly Manchester United's best signing of the summer of 2009
(Image: GETTY)

The day before the Ronaldo deal was confirmed United announced the signature of Wigan Athletic right-back Antonio Valencia for a fee of around £16m.

The Ecuadorian international had impressed with the Latics in the Premier League, and had done enough to convince Sir Alex Ferguson that he could become an important part of the United first-team.

As is usually the case, Ferguson was spot on, and Valencia went on to make a total of 339 appearances over ten seasons before eventually departing in 2019.

He was a leader both on and off the pitch, and consistently delivered the goods for his side, meaning that he was undoubtedly well worth the money spent.

And he was certainly the most successful of the four signings United made that summer by some distance…

2. Michael Owen (signed 3 July)

The world of football was stunned when Michael Owen joined United
(Image: AFP/Getty Images)

Without a doubt one of the most controversial signings in Premier League history, English football was stunned when former Liverpool hero Michael Owen was snapped up on a free by United after his contract with Newcastle expired.

Owen had hardly set the world alight at St James' Park, yet Ferguson was convinced he could still do a job for his side, and such was his faith in the player that he even inherited Ronaldo's No.7 shirt.

The striker went some way towards winning over the United faithful with a dramatic last-gasp winner in a thrilling 4-3 victory over bitter rivals Manchester City that September, but that was one of just three Premier League goals he managed that season.

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He ended up staying three seasons in total but was largely a peripheral figure, particularly in the 2011-12 campaign when he made just four appearances, and that summer he was allowed to leave to join Stoke.

In the end it was a transfer risk which many will feel was not worth it, although that City goal will always be remembered as one of the most iconic of all-time in the fixture between the two great enemies.

3. Gabriel Obertan (signed 8 July)

Gabriel Obertan never made much of an impression at United
(Image: Getty Images)

Another transfer which did not exactly do much to help United fans get over the loss of Ronaldo was that of Gabriel Obertan.

The relatively unknown winger was signed for just £3m from Bordeaux, with Ferguson describing the Frenchman as an "exciting prospect" who they had tracked "for a few years".

Almost immediately Obertan suffered a setback as a spinal issue kept him on the sidelines for a month, but he eventually made his Premier League debut in October against Blackburn.

Ultimately, however, he never quite did enough to earn a regular first-team place, and after two frustrating seasons in which he flattered to deceive and had regular injury problems Obertan was eventually sold to Newcastle in 2011.

He later enjoyed spells at Anzhi Makhachkala, Wigan and Levski Sofia, and currently plays his football at Turkish club Erzurumpspor, but it's fair to say he never hit the heights Ferguson and co were expecting.

4. Mame Biram Diouf (signed 30 July)

Mame Biram Diouf made just nine appearances in all competitions for United

What do you mean, you don't remember Mame Biram Diouf!?

Yes, United's final signing of the summer was yet another one which did not live up to expectations in what was largely an underwhelming transfer market.

Senegalese striker Diouf was signed from Norwegian team Molde but loaned back to them until January, at which point he joined up with his new side and inherited Carlos Tevez's No.32 shirt.

Unfortunately he never played quite as well as the Argentinean did, and after just six appearances in the second-half of the season was sent on loan to Blackburn, where he had a slightly better time of it, playing in 29 games in the 2010-11 campaign.

Ultimately, however, he failed to make the grade, and during the January 2012 transfer window was sold to German outfit Hannover.

Diouf did go on to spend a further six years in England when he represented Stoke between 2014-20, and now 33 years old he has recently signed for Turkish team Hatayspor.

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