Rafael Nadal claimed his fourth U.S. Open Title on Sunday (September 8), bringing him just one win away from a world record. The match – which at first seemed like a sure fire win for Nadal – turned into an almost 5 hour thriller, thanks to his opponent: 23 year-old debut grand slam finalist Daniil Medvedev. Nadal’s victory creeps him closer to Roger Federer on the grand slam ladder: with one more win he’ll match Federer’s record of 20. The 33 year-old lefthander has also become the second oldest U.S. Open champion – behind Australian Ken Rosewall, who was 35 when won in the 70s. In another clash of generations over the weekend, 19 year-old Canadian Bianca Andreescu claimed victory over Serena Williams – the oldest Grand Slam finalist in the Open era. It means Williams fell short of meeting the world record of 24 Grand Slam titles. But Andreescu became the first Canadian to win a tennis major and the first teenager to win a grand slam – since Maria Sharapova in 2006.