9. Novak Djokovic vs. Danii Medvedev (2021)
Rafael Nadal and Roger Federer were the kings of men’s tennis through the 2000s. Then, in 2008, Djokovic came along and brought a new dimension to the game. He soared to the top of the sport and became the World No.1 after a stream of Major wins. In 2021, he had the opportunity to break multiple records. First, he went past Roger Federer’s 310 weeks as World No.1. This was the longest run of the Open Era.
Then, he had the chance to achieve a calendar-year Grand Slam. Rob Slater was the last man to achieve this difficult feat in 1969. After winning Wimbledon, Roland Garros, and the Australian Open, he faced Danii Medvedev in the final. However, Medvedev shocked the world and defeated the Serbian. But it sealed Djokovic’s World No.1 spot for a record seventh time. This took him above Pete Sampras in the all-time rankings (via EuroSport).