Most surprising tennis matches in history

This match is remembered for the incredible upset caused by Roberta Vinci's victory over Serena Williams in the 2015 US Open semifinals. Vinci, an unseeded player, defeated the world number one, preventing Serena from completing the calendar Grand Slam, a feat almost unthinkable at the time.

This match is remembered for its dramatic five-set development and the exceptional quality of tennis displayed by both players. Nadal's victory over a peak Federer on grass, a surface dominated by the Swiss, was a historic milestone that redefined their rivalry.

This match is remembered for its record-breaking duration of almost five hours and Mats Wilander's victory over then-world number one Ivan Lendl. The intensity of the five-set encounter makes it a landmark in tennis history due to its drama and the high level of play displayed by both competitors.

This match is renowned for Novak Djokovic's incredible comeback, as he managed to win after being two sets to love down and saving two match points in the fifth set against Roger Federer. The intensity and high level of play displayed by both tennis players over four hours make it a memorable milestone in tennis history.

This match is a landmark in tennis history due to its dramatic unfolding and the intense rivalry between two legends. It featured a 34-point fourth-set tie-break where McEnroe saved multiple match points, making it an unforgettable spectacle. Borg's victory secured his fifth consecutive Wimbledon title, cementing his legacy in an encounter that redefined expectations for a Grand Slam final.

This match exemplifies one of the most intense and high-quality rivalries in women's tennis history. Chris Evert's 6-3, 5-7, 7-5 victory over defending champion Martina Navratilova was a dramatic and memorable outcome. Evert secured her record sixth French Open title in an encounter that kept spectators on the edge of their seats until the very last point.

This match is a landmark in tennis history due to its incredible progression, with four sets decided by tie-breaks and no service breaks. The intensity and quality of play displayed by two legends like Sampras and Agassi make it an unforgettable encounter. The absence of service breaks throughout the entire match is a rarity that underscores the mastery of both players in serving and returning.

This match is a landmark in tennis history as it was Rafael Nadal's first and only defeat at the French Open up to that point, breaking his 31-match unbeaten streak. Robin Söderling's victory against the 'King of Clay' was a completely unexpected result that shocked the sports world.

This match is a landmark due to the unexpected defeat of Pete Sampras, a seven-time Wimbledon champion, against an unknown Swiss player ranked 145th in the world. George Bastl's five-set victory in the second round of Wimbledon 2002 represented an iconic moment in tennis history, marking Sampras's final appearance at the tournament he had dominated.

This match is remembered for Denis Istomin's shocking victory, as the world No. 117 defeated Novak Djokovic, then world No. 2 and defending Australian Open champion. Djokovic's second-round loss, after nearly five hours of play, was a completely unexpected result that stunned the tennis world.

This match is remembered for the shocking defeat of Roger Federer, a seven-time Wimbledon champion and then world No. 3, by Sergiy Stakhovsky, ranked 116th. The Ukrainian's victory broke Federer's streak of 36 consecutive Grand Slam quarterfinals, cementing it as one of the biggest upsets in modern tennis history.

This match is a landmark due to Rafael Nadal's incredible comeback, who, against all odds and two sets down, managed to defeat Daniil Medvedev. The duration of over five hours and the significance of the title (Nadal's 21st Grand Slam) solidify its status as a legendary encounter in tennis history.