At 38, Novak Djokovic has ticked off almost every milestone a tennis player could dream of. Earlier this season, he lifted his 100th ATP title in Geneva, a landmark moment that stood out in a year where Grand Slam victories have eluded him. Just weeks later at Flushing Meadows, he notched his 192nd career win at a hard-court major, eclipsing Roger Federer’s all-time men’s record. Yet even with those achievements, Djokovic still sits behind Jimmy Connors (109 titles) and Roger Federer (103) on the all-time ATP titles list, making his century mark less a finish line than another measure of how far he has already gone.

Despite still trailing Connors and Federer in total titles, Djokovic himself seems uninterested in padding his numbers, and former American pros Sam Querrey and John Isner

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