Men’s tennis in the 21st century has produced some of the most intense and unforgettable battles in the sport’s history. Five-set marathons, match points saved at the last second, legendary rivalries, and moments that changed careers and rankings have defined this era. These matches were not just about trophies — they tested endurance, nerve, and character. For many fans, long Grand Slam nights mean switching between live coverage, match stats, and short breaks online, sometimes even unwinding on platforms like Slotozen Casino before returning to the action. Below are 11 clashes that delivered the highest drama and left a lasting mark on modern tennis.
Marat Safin vs. Andre Agassi, Australian Open 2004, semifinal
By the semi-final of the 2004 Australian Open, Agassi had not lost in Melbourne since 1999, having won three consecutive titles. Safin, meanwhile, was just beginning his comeback after a wrist injury and was unseeded. This was the fourth of four five-set matches he had played in the tournament—he had just defeated Andy Roddick in the quarter-finals, denying him the world number one ranking in the process.
The semi-final was played in the middle of the day under extreme heat. In this match, which has become a classic of hard-court tennis, Agassi — already 33 at the time — had set points in both of the first two sets. After the American managed to come back and even the score at two sets apiece, it seemed nothing could save Safin; he had spent too much time on the court. But Agassi faltered first — in the fourth game of the decisive set, he made a forehand error that proved fatal. Safin advanced to the Australian Open final for the second time in his career, where he lost only to Roger Federer, who was just beginning his historic run.
Guillermo Coria vs. Gaston Gaudio, Roland Garros 2004, final
The first (and so far only) all-Argentine final in Grand Slam history turned out to be one of the strangest finals of the decade. It was contested between unseeded Gaston Gaudio and Guillermo Coria, who had been the top clay-court specialist for two years running. With Federer having lost to Kuerten in the third round and Nadal still largely unknown to the general public, this was the last Grand Slam where the winner did not have to face either of these future legends.
Coria, the overwhelming favourite, won the first two sets with astonishing ease. Then, the unexpected happened: whether due to nerves or sudden dehydration, he was struck by cramps that would torment him until nearly the end of the match. Gaudio seized the opportunity and played like a true finalist, never letting up.
In the fifth set, Coria, barely able to walk on the court, still had two match points—but missed both by mere centimetres. That final marked the end of his appearances at Roland Garros, illustrating how a single match can profoundly impact a career.
Marat Safin vs. Roger Federer, Australian Open 2005, semifinal
Many consider this match one of the greatest hard-court encounters in tennis history. While such claims are always subjective, there is no doubt that the level of quality and tension was exceptional. By this time, Federer had firmly established himself at the top of the game and was the clear favourite. A few months earlier, he and Safin had met in the final of Houston, where Federer had prevailed in two sets after a record-breaking tie-break. Up until then, Safin had beaten Federer only once in six previous encounters.
This semifinal quickly became legendary. In the fourth-set tie-break, Federer had a match point on his serve at 5-3 — but Safin saved it with a perfectly timed lob, one of the very few he attempted in the match. Ultimately, Safin converted his seventh match point and went on to defeat Lleyton Hewitt in the final. Few could have imagined that the 2005 Australian Open would become the last Grand Slam title of Safin’s career.
Rafael Nadal vs. Roger Federer, Wimbledon 2008, final
This match is often hailed as one of the greatest tennis matches of all time. While “all-time” is always open to debate, in the Open Era, few matches have matched its intensity, drama, and sheer significance.
The clash of titans on Centre Court was as much psychological as it was physical. Nadal, already established as Federer’s nemesis, seemed poised to storm Wimbledon and claim a routine victory in the first two sets. But then a combination of nerves, swirling wind, and the encroaching darkness allowed Federer to mount a comeback, taking the third and fourth sets and even saving two match points in the fourth-set tie-break.
Yet the decisive fifth set, played almost entirely in darkness, belonged to Nadal. The Spaniard prevailed, ending Federer’s five-year reign at Wimbledon and claiming not only the championship but also the world number one ranking. The match remains an enduring testament to resilience, skill, and the fine margins that define tennis history.
Rafael Nadal vs. Fernando Verdasco, Australian Open 2009, semifinal
In terms of pure quality, this was one of the best matches on the list. Few expected Verdasco to reach the semi-finals, yet the all-Spanish clash pushed Nadal to his first Grand Slam final on hard court. It was also the last year the Australian Open was played on the Rebound Ace surface.
The two left-handers delivered a true tennis spectacle, mixing relentless attack with stubborn defence. Verdasco, playing arguably the best tennis of his career, stayed aggressive throughout and struck 95 winners in a marathon match that lasted five hours and 14 minutes. This was the closest he ever came to defeating Nadal.
The fourth-set tiebreak, which Verdasco dominated 7–1, was outstanding. But in the decisive moments, nerves proved decisive. Serving at 4–5 in the fifth set, he handed Nadal the match with a double-fault.
Nadal went on to defeat Federer in the final, capturing his first of two Australian Open titles.
Roger Federer vs. Juan Martin del Potro, Roland Garros 2009, semifinal
Nadal’s unexpected fourth-round exit at Roland Garros in 2009 seemed to clear the path for Federer to finally win the title. Still, the journey was far from easy.
In the fourth round, Federer had to recover from two sets down against Tommy Haas. In the semi-final, he again found himself in trouble, trailing 2-1 in sets to Juan Martín del Potro.
It was the Argentine’s second Grand Slam semifinal. Earlier that season, he had faced Federer in the Australian Open semifinal and lost in straight sets. This time, he pushed Federer to the limit. Del Potro dominated much of the early exchanges, overpowering Federer with heavy groundstrokes and controlling the rallies through the first three sets.
Federer ultimately survived thanks to his experience, fitness, and composure in the key moments. Compared to this battle, the final against Robin Söderling felt almost straightforward.
For Del Potro, however, this match proved to be a sign of what was to come. Later that year at the US Open, he again faced Federer in a five-set thriller — this time in the final — and came away with the biggest win of his career.
Roger Federer vs. Andy Roddick, Wimbledon 2009, final
With Nadal absent due to knee problems after Roland Garros, Andy Roddick reached his first Grand Slam final in three years and had a real chance to challenge Roger Federer.
Roddick played some of the best tennis of his career. He won the first set and then held four set points in the second-set tiebreak. A two-set lead was within reach. But he could not convert. The most painful moment came on an easy high volley at set point, which he missed. He then lost six straight points and let Federer escape.
The match turned into a marathon. It lasted 77 games and ended 16–14 in the final set. Remarkably, the last game was the only one in the entire match that Roddick lost on his serve.
Federer, fresh from winning his only Roland Garros title a month earlier, saved break points under pressure and stayed composed in the decisive moments. With this victory, he broke Pete Sampras’ record for most Grand Slam titles and returned to world No. 1.
Novak Djokovic vs. Roger Federer, US Open 2010, semifinal
This was the first of two almost identical semifinals that Djokovic and Federer played at the US Open in 2010 and 2011. On both occasions, Djokovic won in five sets on Arthur Ashe Stadium — a court where, since 2007, he had repeatedly lost to Federer.
The match itself was uneven in quality. Both players struggled for consistency and only produced their best tennis in the deciding set. The key moment came at 4-5, when Djokovic faced two match points on his serve. Instead of playing safe, he struck two fearless forehands and saved both, shifting the momentum completely.
Much has been said about Djokovic’s breakthrough season in 2011, often linked to Serbia’s Davis Cup victory in 2010. But if one moment marked the true turning point, it was those two saved match points and his first win over Federer on this stage. The victory gave him belief that he could beat the very best under pressure.
Djokovic later lost the final to Nadal, but the psychological foundation for his future dominance had already been built.
Roger Federer vs. Novak Djokovic, Roland Garros 2011, semifinal
This match is remembered not only for its high level of tennis or its historical weight, but also for one iconic moment. After sealing victory with an ace on match point, Federer raised his finger in the air, a quiet gesture that showed he still had plenty left in the tank.
It turned out to be the only Grand Slam match Djokovic lost in 2011. He came close to staging a comeback from two sets down and even served for the fourth set as darkness fell over Court Philippe Chatrier. Had he leveled the match, play would almost certainly have been suspended until the next day, and the outcome might have been very different.
But Federer, who later said it was the best clay-court match of his career, played with total focus. He ended Djokovic’s remarkable winning streak, which had already passed 40 matches. Fittingly, that streak had begun with a loss to Federer at the 2010 Tour Finals — and it also ended against Federer.
Novak Djokovic vs. Rafael Nadal, Australian Open 2012, final
Right after the match, many called it the best and most dramatic Grand Slam final of the decade. Such claims are always subjective, but one fact is undeniable — it lasted five hours and 53 minutes, making it the longest major final in the Open Era.
Djokovic eventually won after trailing 4-2 in the deciding set. The match was full of tension and momentum swings. By the fifth hour both players were physically exhausted, yet the quality of tennis in the final stretch remained surprisingly high.
The achievement was even more impressive considering that two days earlier Djokovic had also played a five-set semi-final against Andy Murray. Across those two matches, he spent nearly 11 hours on court. It was a clear display of endurance, resilience, and mental strength.
With this victory, Djokovic secured his third consecutive Grand Slam title and strengthened his position as world number one, confirming his dominance at the very top of the game.
Rafael Nadal vs. Novak Djokovic, Roland Garros 2013, semifinal
The semifinal between Novak Djokovic and Rafael Nadal at Roland Garros turned into a true thriller — exactly what fans expected from this rivalry. Nadal had just returned after missing more than six months with knee problems and immediately showed top form, reaching eight finals in his first eight tournaments back on tour. Djokovic, who at the time led the world rankings, had already beaten Rafa earlier that spring, denying him a ninth Monte-Carlo title.
The pre-match atmosphere was even more emotional due to a personal tragedy. A few days earlier, Djokovic’s first coach, Jelena Genčić, had passed away. He often described her as a second mother and was determined to complete his Career Grand Slam in her memory.
The clash was widely billed as the match of the year even before it started. Tennis Channel scheduled its broadcast at 7:00 am ET in the United States, treating it almost like a Super Bowl. The players lived up to the hype, delivering another classic that lasted four hours and 37 minutes.
Nadal served for the match in the fourth set but failed to close it out. In the fifth, he fell a break behind and stood on the edge of defeat. Still, he fought back to win his 58th match out of 59 at Roland Garros and advanced to his eighth final. After the handshake, Nadal thanked the crowd and first asked them to applaud his opponent — a gesture that summed up the respect between the two champions.