No. 1 seed Casper Ruud of Norway and No. 2 seed Hubert Hurkacz of Poland both reached the semifinals of the Millennium Estoril Open with victories Friday in Portugal.

Ruud converted 3 of 5 break-point opportunities on his way to defeating Hungary's Marton Fucsovics 6-3, 6-2. Fucsovics was fighting through an injury throughout the match.

Hurkacz had to pull out a tiebreaker win before besting Spanish qualifier Pablo Llamas Ruiz 7-6 (4), 6-4. Hurkacz went 8-for-8 saving break points, including five in the first set, when the players held serve all the way to 6-6.

In the semifinals, Ruud will face Pedro Martinez of Spain -- a 6-4, 6-4 winner over lucky loser Richard Gasquet of France -- while Hurkacz will meet Chilean Cristian Garin, who ended the home-soil run of Portugal's Nuno Borges with a 6-2, 7-6 (3) result.

Grand Prix Hassan II

Playing on a protected ranking, Matteo Berrettini defeated fellow Italian and fourth seed Lorenzo Sonego 6-3, 7-6 (5) to advance to the semifinals in Marrakech, Morocco.

The 2021 Wimbledon finalist is playing just his second event of the season, but he managed to win an overwhelming 83.6 percent of his first-serve points (46 of 55) and hit five aces to beat Sonego.

That result left No. 7 seed Mariano Navone of Argentina as the only seeded player left standing. Navone beat Australian Aleksandar Vukic of Australia 6-2, 6-4. Berrettini will face Navone in one semifinal, while Russia's Pavel Kotov will meet Spaniard Roberto Carballes Baena in the other.

Kotov cruised past Italian qualifier Fabio Fognini 6-1, 6-2, while Carballes Baena beat American qualifier Nicolas Moreno De Alboran 6-4, 4-6, 6-4.

U.S. Clay Court Championship

Top-seeded Ben Shelton won an all-U.S. quarterfinal in Houston, beating Brandon Nakashima 7-5, 7-6 (9).

Shelton got the only service break of the first set in the final game. In the second set, Shelton failed to take advantage of two match points at 4-5. The tiebreaker included two set points for Nakashima before Shelton ultimately prevailed on his fifth overall match point.

Shelton's semifinal foe will be fourth-seeded Tomas Martin Etcheverry of Argentina, who advanced when the United States' Michael Mmoh retired while trailing 6-3, 0-1.

The other semifinal will feature third-seeded Frances Tiafoe of the United States and Italy's Luciano Darderi. Defending champion Tiafoe got past sixth-seeded Jordan Thompson of Australia 7-6 (8), 6-4, and Darderi upset seventh-seeded Marcos Giron of the United States 6-0, 6-4.

--Field Level Media