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August 8, 2026
Ronaldo's career appears perfectly mapped out in hindsight, but several major decisions could have sent it in completely different directions. From nearly joining Arsenal to resisting Real Madrid for another year and almost signing for Manchester City, these were the crossroads that shaped the CR7 story...
Cristiano Ronaldo's journey from Madeira to football immortality can look almost inevitable when reduced to a list of clubs: Sporting CP, Manchester United, Real Madrid, Juventus, Manchester United again and Al-Nassr. The reality was considerably messier. Deals collapsed, managers intervened and Ronaldo himself changed course at decisive moments. That unpredictability is part of what keeps football so compelling, whether fans are debating transfers, match outcomes or following platforms such as winbuzz bet alongside the action. Some alternatives came remarkably close to happening. Had only one gone differently, not just Cristiano Ronaldo's career but the histories of several of Europe's biggest clubs might have changed with it.
Different backgrounds but a common passion! pic.twitter.com/fp43D7xYQb
— Cristiano Ronaldo (@Cristiano) May 24, 2026
The first major fork in Ronaldo's career arrived before most football supporters outside Portugal knew his name.
Arsène Wenger pursued the Sporting teenager seriously. Ronaldo visited Arsenal's training ground and later described himself as having been extremely close to joining the club. Wenger subsequently explained that Arsenal could not compete once Manchester United were prepared to meet Sporting's asking price. Liverpool were interested too, with former manager Gérard Houllier later saying the club backed away partly because Ronaldo's proposed wages would have disrupted its salary structure.
Then came Sporting's famous August 2003 friendly against Manchester United. Sir Alex Ferguson moved quickly afterwards, and Ronaldo has said Ferguson personally helped persuade him that Old Trafford was the right destination.
Imagine the alternatives. Ronaldo developing alongside Thierry Henry at Arsenal, or arriving at Liverpool just before Rafael Benítez's Champions League-winning era, would have rewritten Premier League history before his own legend had properly begun.
Ronaldo eventually joined Real Madrid in 2009, but his move could easily have happened one year earlier.
After winning the Premier League and Champions League with United in 2007/08, Ronaldo made little secret of his attraction to Madrid. The transfer saga dominated that summer and reached the point where his departure appeared increasingly plausible.
Ferguson travelled to Lisbon for a conversation with his star player. Ronaldo later confirmed that he accepted the manager's argument and chose to remain at United for the 2008/09 season, insisting it was his own decision rather than one forced upon him.
That extra year mattered. United won another Premier League title and reached another Champions League final. Ronaldo then left in 2009 for a world-record £80 million (€94 million).
Had he forced the transfer through in 2008, one entire final chapter of his first United spell disappears.
If moving to Madrid was predictable, leaving it in 2018 was anything but.
Ronaldo had just helped Real win a third consecutive Champions League and a fourth in five seasons. He was the club's all-time leading scorer and remained central to Europe's dominant team.
Yet within weeks he was a Juventus player.
Ronaldo later explained that his relationship with president Florentino Pérez had changed and that he no longer felt valued in quite the same way. Juventus offered a new challenge, and Madrid agreed to let one of the greatest players in its history leave.
This may be the most intriguing footballing “what if” of the lot. Ronaldo continued scoring heavily in Italy, while Madrid initially struggled without him before eventually rebuilding. What if the partnership had lasted another two or three years? Given what Madrid subsequently achieved in Europe, the potential trophy count is impossible to ignore.
The strangest Ronaldo timeline might be the one in which he wears Manchester City's shirt.
When he decided to leave Juventus in August 2021, City became a genuine possibility. Ronaldo himself later said the move had been close and that City had pushed to sign him, although people on the City side subsequently disputed just how advanced the deal really was.
Then Manchester United entered the race.
Ferguson again played a role, and within hours the story had flipped from Ronaldo potentially joining United's local rival to one of Old Trafford's most emotional homecomings.
The reunion produced 24 goals in his first season but ultimately ended badly following tensions under Erik ten Hag and Ronaldo's explosive 2022 interview.
A City move raises irresistible questions. How would Ronaldo have fitted into Pep Guardiola's system? Would City still have pursued Erling Haaland a year later? And what would United supporters have made of their former No.7 playing in sky blue?
Ronaldo's final great crossroads came after Manchester United terminated his contract in November 2022.
At 37, he could attempt to remain in European football or accept a radically different challenge. On December 30, Al-Nassr announced his signing on a contract initially running until 2025.
The move initially looked like an epilogue. Instead, it became a starting gun.
Saudi football subsequently attracted a wave of high-profile players, and Ronaldo became the league's most recognisable global figure. More importantly, he did not treat the move as a short farewell tour. In June 2025, he extended his Al-Nassr contract until 2027, committing himself to the club beyond his 42nd birthday.
That decision offers the clearest lesson from Ronaldo's career. Its extraordinary shape was never completely pre-written.
Arsenal almost had him. Madrid almost got him a year earlier. He could have remained at the Bernabéu. Manchester City nearly became his destination. Europe might have remained his home after 2022.
At every turn, one decision opened a new version of Cristiano Ronaldo — and closed another that football will never get to see.
Cristiano Ronaldo next game for Al Nassr is on August 16, against Al Diriyah, for the King's Cup. You can watch Al Diriyah vs Al Nassr, Ferencvaros vs Real Madrid, Barcelona vs Nottingham Forest, Manchester United vs PSG, Chelsea vs AC Milan and Bayern Munich vs Aston Villa, all matches provided from our live football game pages.
Al Nassr next game:
Al Nassr vs Al Diriyah kick-off time (16-08-2026):
Beijing (China) | UTC/GMT+8: 03:00
India (New Delhi) | UTC/GMT+5.30: 00:30
Saudi Arabia (Riyadh) | UTC/GMT+4: 23:00
Spain (Madrid) | UTC/GMT+2: 21:00
Portugal and England (Lisbon/London) | UTC/GMT+1: 20:00
Rio de Janeiro (Brazil) | UTC/GMT-3: 16:00
New York (United States) | UTC/GMT-4: 15:00
Los Angeles (United States) | UTC/GMT-7: 12:00
Sources: ronaldo7.net / espn.com / skysports.com
