Ugo Carabelli has been the luckiest—and hardest-working—loser in tennis the past couple of months. In Rio in February, the Argentine lost in qualifiers, but made it into the main draw after another player pulled out. By week’s end, he had reached his first 500 semifinal. The next week in Santiago, he made another semi. In Miami, he went the lucky loser route again. This time he has made the most of it by beating two Americans, Brandon Holt and Alex Michelsen, in three-set comebacks.

All of that has taken the 25-year-old dirt-baller to a career-high ranking of No. 61, and a meeting with Novak Djokovic in the third round of a Masters 1000 on hard courts.

Will this be the end of his “lucky” run? Djokovic is a six-time champion in Miami, but as intimidating as that sounds, Carabelli will also know that he hasn’t been his usual self in 2025. On Friday, Djokovic beat Rinky Hijikata, but the second set went to a tiebreaker. If Carabelli can bring his scrappy clay game to bear on these courts, and make Djokovic hit a ton of balls, he could get under the old guy’s craw. Winner: Djokovic—Steve Tignor

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