If three up-and-coming Americans losing in the first round of Atlanta on Tuesday stung, the way they lost hurt even worse. Two of the players dropped third-set tiebreakers, while another lost eight match points in his second set before succumbing in three.

Perhaps none of the losses was more heartbreaking than 19-year-old Reilly Opelka’s 5-7, 7-6 (14), 6-1 defeat at the hands of world No. 72 Malek Jaziri. Opelka made the semifinals in Atlanta last year.

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The 6-foot-11 Floridian held eight match points in the second set, including two on his own serve in the second-set tiebreaker. After earning four opportunities to close it out as Jaziri served at 5-6 in the set, he failed to convert on four more in the tie-breaker.

Opelka certainly wasn’t the only one to leave the court gutted, though. Frances Tiafoe, the youngest player in the Top 100, served for the match against world No. 174 John Millman before losing, 5-7, 6-4, 7-6 (5) in two hours and 19 minutes.

The way he gave the break back was possibly the toughest as all, as Tiafoe bounced a high volley from the service line before the net.

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If that wasn’t enough, world No. 117 Bjorn Fratangelo also lost third-set tiebreaker, to Canadian Vasek Pospisil, 7-5, 4-6, 7-6 (3) in the second-longest match of the day behind Jaziri-Opelka, taking two hours and 39 minutes.

Two Americans advanced, with wildcard Christopher Eubanks defeating compatriot Taylor Fritz, 7-6 (5), 6-4, and sixth-seeded Donald Young cruising past fellow American Tim Smyczek, 6-4, 6-2.

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