Bruised and battered, Novak Djokovic makes incredible history at U.S. Open

The 24-time major winner also became the fourth-oldest man to advance to a U.S. Open quarterfinal, trailing only Pancho Gonzales, Ken Rosewall and Jimmy Connors. In 1991, Connors, just two weeks before turning 39, famously reached the semifinals of his home major. Djokovic, born in 1987, is trying to replicate the American's feat.

"I remember that [Connors 1991] run," Djokovic said. "I was very, young, so I don't vividly remember it when it was happening. But in the years to come, when I was growing up watching a lot of tennis, everyone was talking about that run being one of the most historic runs we had in the sport at any Slam.... Just being in the same discussion or same conversation with Jimmy is obviously a huge honor of mine."

Djokovic needs three more wins to equal Connors, Roger Federer and Pete Sampras for most U.S. Open titles in the Open Era. 

Unfortunately for the Serb, his chances of catching the trio are very slim, considering his recent injury history and head-to-head record against Jannik Sinner, the defending champion at Flushing Meadows. Djokovic was forced to retire from the Australian Open due to medical reasons and lost in straight sets in back-to-back semifinals to Sinner at Roland-Garros and Wimbledon. In both losses to Sinner, he needed multiple medical timeouts to deal with a wide array of issues.

To make matters worse, Djokovic has been hobbled through the first week at the U.S. Open. In the first round against Learner Tien, he dealt with a toe injury, and in the third round, he needed two medical timeouts to treat back spasms. 

It would be nothing short of a miracle if the bruised and battered Djokovic can survive Fritz, Carlos Alcaraz (potential semifinal) and Sinner (potential final) and lift the trophy on Sunday. But if he does, he will only strengthen his case as the greatest of all time.