Roger Federer, a name synonymous with elegance and unparalleled skill, has left an indelible mark on the world of tennis. For over two decades, the Swiss Maestro was a dominant force, amassing accolades and victories that placed him among the greatest ever, rivaled only by the legendary Jimmy Connors in terms of trophies and holding the record for third-highest prize money earned in the sport.

As the curtain closed on his remarkable career in 2022, tennis fans were left reminiscing about the iconic matches that defined his path to greatness. One such highlight was the breathtaking 2008 Wimbledon final against Rafael Nadal, a match that is rightly celebrated as one of the greatest in tennis history.

Let’s delve into five of Roger Federer’s most pivotal victories that not only shaped his career but also the landscape of tennis itself.

#5 Roger Federer vs Pete Sampras, Wimbledon 2001

Stepping onto the hallowed grass of Wimbledon in 2001 as the 15th seed, Federer was a promising star on the rise. Having just claimed his first ATP title earlier that year in Milan, he was ready to make his mark.

His journey through the tournament was impressive as he bested players like Christophe Rochus, Xavier Malisse, and Jonas Bjorkman, setting up a much-anticipated clash with the legendary Pete Sampras, a four-time defending champion and the tournament’s top seed.

In a match that promised fireworks, it was the 20-year-old Federer who struck first, clinching the opening set in a tense tiebreak. Sampras responded by snagging the second, but the match’s excitement surged into a deciding fifth set. Maintaining his poise, Federer edged out a 7-5 victory in the final set, though he ultimately bowed out to Tim Henman in the ensuing quarter-finals. This victory, however, catapulted him into the spotlight and earned him respect within the tennis community.

#4 Roger Federer vs Mark Philippoussis, 2003 Wimbledon

By the time Wimbledon 2003 rolled around, Federer had established himself as a formidable force in men’s tennis, having peaked at World No. 6 the previous year. Nevertheless, a Grand Slam title eluded him.

As the fourth seed, he cruised through the rounds, defeating notable opponents such as Lee Hyung-Taik and Andy Roddick in the semifinals. The final saw him paired against big-serving Australian Mark Philippoussis. Federer exhibited remarkable composure in his first Major final, sweeping Philippoussis aside in straight sets, thereby officially announcing himself as a premier contender in the sport.

#3 Roger Federer vs Tommy Haas, 2009 French Open

Heading into the 2009 French Open, Federer was already a 13-time Major champion but had yet to capture the elusive title at Roland Garros. Struggling in recent Grand Slam tournaments—particularly with losses to Rafael Nadal—he needed a breakthrough.

In a twist of fate, Nadal was upset in the fourth round, clearing Federer’s path. After navigating through the early rounds with ease, Federer faced Tommy Haas. In a gripping contest, Federer initially found himself down two sets. However, demonstrating his trademark resilience, he turned the match around, winning in five sets, including a decisive bagel in the fifth. This victory set the stage for him to capture his 14th Major title by defeating Robin Soderling in the final.

#2 Roger Federer vs Rafael Nadal, 2017 Australian Open

Following a knee injury that forced Federer to end his season prematurely in 2016, he returned for the 2017 Australian Open as the 17th seed—the lowest he had been ranked in a Major in nearly 15 years.

In a stunning turn of events, Federer defied the odds and reached the final, overcoming formidable opponents like Stan Wawrinka and Kei Nishikori. In the finale, he faced his long-time rival, Rafael Nadal, in a clash that was highly anticipated by fans worldwide.

The match unfolded like a classic, swinging dramatically back and forth, particularly in a gripping fifth set. After falling behind 3-1, Federer showcased his relentless spirit and won five straight games to clinch his 18th Grand Slam title, sealing a remarkable comeback.

#1 Roger Federer vs Marin Cilic, Australian Open 2018

With a resurgent season behind him in 2017 that featured two Grand Slam titles, Federer entered the 2018 Australian Open buoyed by expectations. Remarkably, he had navigated the tournament without dropping a single set.

His final opponent, Marin Cilic, was a familiar one, having faced Federer in the Wimbledon final the previous year, where the Swiss emerged victorious in straight sets. However, this time around, Cilic put up a fight, pushing the match to a decisive fifth set. Undeterred, Federer maintained his composure and closed out the match 6-1 in the final set, etching his name in the record books as the first male player to reach 20 Grand Slam titles.

Through these unforgettable matches, Roger Federer not only carved a niche for himself in tennis history but also set the standard for future generations. His legacy will undoubtedly resonate for years to come.