Roger Federer: Five matches that defined the retiring tennis legend's career

On Thursday 15 September, tennis legend Roger Federer announced he will retire from the sport with his final match due to take place at the Laver Cup on Friday 23 September.

The 41-year-old Swiss maestro leaves the game an all-time great, with 20 Grand Slam titles, an Olympic gold medal, 310 weeks as World No. 1 and a reputation as one of - if not the - greatest proponents of the game.

But even with well over 1,000 matches under his belt, there are some moments that stand above others in defining the greatness of this tennis sensation. Here are five of the most important matches in the history of Federer’s career.

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Wimbledon 2003: First Grand Slam title

As with so many of his greatest triumphs, Federer’s first Grand Slam title came on the grass courts of the All England Club, in the final of Wimbledon in 2003. Expectation had been high that the 21-year-old Swiss would turn his immense promise into Grand Slam titles, but before this tournament, his best performances had been reaching the quarter-finals in Wimbledon and the French Open in 2001.

Wimbledon 2003 saw him face up against the unseeded Australian Mark Philippoussis in the final, having already bested tournament favourite Andy Roddick in the semis. Philippoussis’ main weapon was his huge serve, but Federer showed maturity beyond his years to take a straight sets win that included two tie breaks - the second of which handed him a 7-6, 6-2, 7-6 victory.

"I was always joking when I was a boy that I would win this," Federer said after the match, as his childhood dreams became a reality. Little did he know that this would just be the first major title in a tennis career that will end this week with 20 Grand Slam titles.

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Beijing 2008: Olympic doubles gold

By the time Federer took to the courts at the Beijing 2008 Olympics, he was already a vastly different animal than the young prospect who secured his first Grand Slam title five years before. Three Australian Open, five Wimbledon and four US Open titles had followed, but just months before the Games the star revealed he had been diagnosed with mononucleosis which left him struggling to regain full fitness.

And 2008 was also a year that saw Federer come out on the losing side of a Wimbledon final dubbed the greatest tennis match of all time, where he succumbed to Spain’s Rafael Nadal 6–4, 6–4, 6–7(5–7), 6–7(8–10), 9–7 after a gruelling four hour and 48-minute marathon.

In the Beijing 2008 singles tournament, a below-par Federer lost in the quarterfinals to the USA’s James Blake to leave his dreams of gold in tatters. However, standing alongside his friend Stanislas Wawrinka, Federer produced a dominant 6–3, 6–4, 6–7, 6–3 victory in the final of the doubles against Sweden's Simon Aspelin and Thomas Johansson to take his place on the top step of the podium.

“It’s a dream come true moment. It comes around maybe once in a lifetime,” Federer stated after the match. It was a prediction that proved to be a true one, as the closest he came to singles gold would be the silver he won four years later at London 2012.

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French Open 2009: Career Grand Slam

While Federer has won eight Wimbledon, six Australian Open and five US Open titles in a 19-year span, he only has one French Open title to his name. Much of that is down to the dominance of Spain’s Nadal on the clay courts and the 14 victories he has amassed at Roland Garros between 2005 and 2022.

However, in 2009 Federer created history, becoming only the sixth man ever to win all four Grand Slams when he defeated Sweden's Robin Soderling 6-1, 7-6, 6-4 in wet conditions in the French Open final.

Soderling had surprisingly beaten Nadal in the fourth round, but was no match for Federer in the title-deciding match, stating afterwards that the Swiss maestro had taught him a “lesson how to play.”

Federer declared the match his “greatest victory” and showed his relief by stating “I can now go the rest of my career without worrying that I would never win the French Open.”

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Wimbledon 2017: Eighth Wimbledon title

Having won seven Wimbledon titles between 2003 and 2012, Federer’s dominance of the grass courts and Grand Slam tournaments had seemed to be on the wane. Five years went by without the now veteran athlete winning a Grand Slam title - but all that would change in 2017 when a resurgent Federer returned to his favourite stomping ground in London.

14 years after his first Wimbledon victory, a 35-year-old Federer blew away the challenge of the injury-stricken Marin Cilic to record a 6-3, 6-1, 6-4 victory in front of a thrilled centre-court crowd.

It was perhaps as dominant a win as he ever secured in his legendary career.

“It’s magical,” a thrilled Federer stated after the final. “I can’t believe it yet. It’s too much. I kept on believing and dreaming and here I am today for my eighth title.”

Australian Open 2018: 20th Grand Slam title

Federer had been going through a purple patch when he lined up in the Australian Open final of 2018. Two Grand Slam victories in the previous year, at Wimbledon and the Rod Laver Arena, saw the Swiss star aiming to defend his title in Australia and add a third Grand Slam title in a year to his resume.

Victory would also put Federer into a league of his own, as the first man in history to win 20 Grand Slam titles. And standing in his way once again was Croatia’s Cilic, the opponent he had breezed past in straight sets just the previous year at Wimbledon.

However, this match would prove to be one of the hardest-fought title wins of Federer’s career.

After dominating the first set 6-2, Cilic bounced back to win the second and fourth leaving a final decider to define the champion.

However, under a closed roof, Federer stormed into a 3-0 lead in the final set, seeing out the match 6-2, 6-7, 6-3, 3-6, 6-1 to secure an unprecedented 20th Grand Slam.

At the time, nobody could have foreseen that this title would be the last Grand Slam the dominant Swiss would win in his career. But it stands as a timely reminder of the nerveless skill and ‘never-give-up’ attitude of a man who will go down in history as one of the best tennis players the game has ever produced.