Cristiano Ronaldo's complex Arsenal relationship: From failed move to hushing fans and beyond

To many, the intense rivalry between Manchester United and Arsenal that dated from the late nineties through to the early noughties is the defining battle of the Premier League era.

Sir Alex Ferguson vs Arsene Wenger, Scottish steel up against French flair – the two sides would often break out into fights seemingly every time they met.

But amid all the flaring tempers and tunnel tantrums, a superstar was emerging ever so quietly in the form of Cristiano Ronaldo.

Little more than a footnote in the story of the two club’s contests of the time, the likes of Thierry Henry, Ruud van Nistelrooy, Patrick Vieira and Roy Keane were the defining match-ups of the time.

Though Arsenal are often rightly credited as a club that has always given youth a chance, United had two young stars within their ranks from 2004 onwards that would go on to shake the Premier League to its very core.

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Cristiano Ronaldo was part of the ‘Battle of Old Trafford’ against Arsenal in 2003

One Ronaldo, the other of course a man who would go on to be United’s record goal-scorer in Wayne Rooney – for a fairly lengthy period of time, everyone associated with Arsenal would have been sick of the sight of both of them.

However, analysing Ronaldo’s tricky relationship with the red half of north London alone, we must start at the very beginning; before he touched down on Manchester soil as a gangly teen donning some questionable knitwear.

As Arsenal prepare to travel to United for what promises to be another pivotal contest in the race for Champions League qualification, here are Ronaldo’s most notable moments against the Gunners.

The move that never was

Sir Alex Ferguson signed Cristiano Ronaldo from Sporting Lisbon in 2003, pipping Arsenal to the post


John Peters/Manchester United via Getty Images)

While it is likely little more than a mildly amusing anecdote for the more smug members of the United faithful, Arsenal fans are surely sick of hearing about how they could have been the ones to bag Ronaldo.

Wenger has never been particularly shy of revealing a whole host of elite talent he nearly signed, but he undoubtedly mentions the Ronaldo saga the most.

Recently pressed on the player he regrets not signing the most, the Frenchman conceded to talkSPORT : “At that time it was [Cristiano] Ronaldo.

“He played at Man United in 2004, and he’s one of the players I regret not to have signed because we were very close.”

Having made waves with his performances for boyhood club Sporting, Ronaldo was being monitored by a number of top clubs across Europe; including Arsenal and United.

The story goes that both Wenger and then-vice Chairman of Arsenal David Dein met a teenage Ronaldo in a restaurant alongside his agent, on the cusp of sealing the deal – the Gunners let the teenager go home and think about it.

It proved to be a fatal mistake, with United nabbing the forward’s signature from under the noses of the club who was most certainly back then their most fierce rival.

That night at Highbury

Cristiano Ronaldo wheels away in celebration with Ryan Giggs

Though Ronaldo has previously stated his respect for Arsenal as a club, he paid them very little during a trip to Highbury in 2005.

Another game between the two sides where Ronaldo’s influence is often forgotten, the Portugal star actually bagged a brace as United registered a dramatic 4-2 victory over the Gunners.

A fixture best remembered for Keane and Vieira’s infamous spat in the Highbury tunnel, Ronaldo’s goal-scoring heroics actually fell behind both the pre-match controversy and the stunning sight of John O’Shea deftly chipping Manuel Almunia as a talking point.

However, the contest could be viewed as a defining point in Ronaldo’s United career as the first time he delivered in a huge tie.

Ronaldo had got the backs up of every Arsenal fan early on after he dared to square up to Gunners icon Thierry Henry, ensuring he was jeered for the remainder of the contest.

With Arsenal leading 2-1, Ronaldo scored twice in four second half minutes to turn the match on its head.

Following his second, Ronaldo hushed the Highbury crowd – silencing the boos the way he so often does 16 years on.

2007/08 heroics

Cristiano Ronaldo places his penalty beyond the dive of Arsenal goalkeeper Jens Lehman

The 2007/08 Premier League season was the campaign that saw Ronaldo truly transform into one of the world’s best – as Arsenal found out the hard way.

The Portugal skipper netted a staggering 42 times in 49 appearances across all competitions, but he enjoyed a particularly successful time of it against the Gunners.

Notching against Arsene Wenger’s side in both games home and away, the first came at the Emirates when Ronaldo thought he had won the tie for United nine minutes from time when he made it 2-1 with just nine minutes left.

William Gallas salvaged Arsenal on the day, scoring a last gasp equaliser to rescue a point – but Arsenal were not so fortunate on their travels.

Ronaldo scored United’s leveller in a 2-1 comeback victory over the Gunners at Old Trafford, though the game’s biggest talking point came late on.

Often one for showboating in his younger days, Ronaldo committed one step-over too many in the eyes of Arsenal full-back Justin Hoyte, who rather comically upended the winger due to his frustration.

Silencing the Emirates

Cristiano Ronaldo scores a stunning free-kick away at Arsenal in the second-leg of the 2009 Champions League final

Clearly not content with hushing Highbury, Ronaldo proved to be a thorn in the side of Arsenal in their plush new ground as well.

United put in a number of impressive displays during their route to the 2009 Champions League final in Rome, but their all-English affair with Arsenal at the semi-final stage topped the lot.

Though the Red Devils already boasted a 1-0 advantage from the first-leg, morale was high around the Emirates as a pre-match lightshow set the scene for what many of the Arsenal support hoped to be a memorable night.

It was, but for all the wrong reasons if you are of an Arsenal persuasion.

Ronaldo scored two on the night, but it was his first that lives long in the memory – a free-kick so far out it felt longer than the distance between Arsenal’s old and new stadia.

His second sealed United’s victory and place in the final, though it was to end in heartbreak after a Lionel Messi-inspired Barcelona ran out 2-0 victors on the night.

His overall record against the Gunners

Cristiano Ronaldo has scored six goals against Arsenal over the course of his career

Ronaldo will be aiming to inflict even more damage to Arsenal on Thursday evening, having already scored against them on six different occasions.

All of the goals came while in the colours of United, while his last league meeting against the three-time Premier League winners came in the form of a 0-0 draw in May 2009.

Given the latest meeting comes at Old Trafford, the pre-match omens are not as good as Ronaldo would have liked – the 36 year old netting just once against Arsenal at home, the remaining five coming in the capital.

Arsenal boss Mikel Arteta never had to face Ronaldo during his own playing days in north London, but will know all too well the kind of threat the forward poses to his side.

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