(Photo credit: Mike Frey-Imagn Images)

Alex Molcan, participating in his first ATP Tour-level tournament since 2024, upset top-seeded Gabriel Diallo of Canada 6-2, 6-2 on Wednesday in the second round of the Tiriac Open in Bucharest, Romania.

Molcan, a 28-year-old Slovakian, has fallen from a career-best ranking of 38th four years ago to 189th this week. He came up big in the key moments against Diallo, saving six of the seven break points he faced.

Fourth-seeded Nuno Borges of Portugal also dropped his second-round match, falling 7-6 (1), 6-4 to Bosnia and Herzegovina's Damir Dzumhur.

Seventh-seeded Mariano Navone of Argentina thrashed Denmark's Elmer Moller 6-2, 6-1, and eighth-seeded Botic Van De Zandschulp of the Netherlands defeated Kazakhstan's Alexander Shevchenko 7-5, 6-1.

U.S. Men's Clay Court Championship

Top-seeded Ben Shelton, the 2024 Houston champion, opened play in the event by eking out a 7-6 (5), 7-6 (3) second-round win over China's Zhizhen Zhang.

Shelton, who had a first-round bye in the tournament, finished with a 21-12 edge in aces. Neither player lost his serve in the match, each saving one break point.

Next up for Shelton is a quarterfinal matchup against Argentina's Thiago Agustin Tirante, who trounced the United States' Mackenzie McDonald 6-2, 6-0.

Two other Argentines advanced, as sixth-seeded Tomas Martin Etcheverry came back to beat Australia's Alex Bolt 6-7 (5), 6-0, 6-3, and Roman Andres Burruchaga toppled Australia's Adam Walton 6-2, 6-3.

In the final match of the night, fourth-seeded Tommy Paul of the U.S. nipped Paraguay's Adolfo Daniel Vallejo 3-6, 6-4, 6-4.

Grand Prix Hassan II

Top-seeded Luciano Darderi bested Mattia Bellucci 6-4, 6-2 in an all-Italian second-round match at Marrakech, Morocco.

Bellucci had an 8-2 advantage in aces but never managed a break point on Darderi's serve. Darderi won 14 of his 17 second-serve points to Bellucci's 6 of 25 on that stat, and Darderi converted three of his nine break opportunities.

Argentine qualifier Marco Trungelliti upset fifth-seeded Kamil Majchrzak of Poland 7-6 (4), 6-3. Third-seeded Corentin Moutet of France cruised past Morocco's Taha Baadi 6-0, 6-2, and sixth-seeded Vit Kopriva eliminated Serbia's Hamad Medjedovic 6-7 (4), 7-5, 6-2.

--Field Level Media