AO 2026: Novak Djokovic Clinches 399th Grand Slam Singles Victory With Win Over Francesco Maestrelli, Advances To Third Round

MELBOURNE, Australia — Novak Djokovic dropped a service game for the first time in this Australian Open and then didn't lose another point against Francesco Maestrelli, advancing to the third round with a 6-3, 6-2, 6-2 win.

It was Djokovic's 399th win in a Grand Slam singles match, leaving the 24-time major just one more to be the first player ever to reach 400.

The break of serve, in the sixth game of the third set Thursday, was almost like Djokovic was doing a rehearsal for later matches. He followed a second serve to the net but then missed the volley to give it up.

It stung the 38-year-old Djokovic, a noted perfectionist. He broke Maestrelli at love in the next game to take a 5-2 lead, smacking the last ball into the net after the Italian, ranked No. 141, hit a groundstroke long.

Djokovic held at love in an eight-point roll to finish things off. He's in Australia seeking an 11th title at Melbourne Park and a 25th major overall, which would make him the most decorated tennis player of all time.

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“I didn’t know much about him until yesterday,” Djokovic said of the 23-year-old Maestrelli, who advanced through qualifying to make his Grand Slam main draw debut. "Nevertheless, respect is always there. I don’t underestimate anyone.

“He’s got a big serve. He’s got a big game. He’s lacking experience on the big stage but he's got the game to go high."

In the third round, Djokovic will meet Botic Van de Zandschulp, who beat Shang Juncheng 7-6 (6), 6-2, 6-3.

Keys to success

Defending champion Madison Keys was down a double break in the second set before rallying to beat fellow American Ashlyn Krueger 6-1, 7-5.

“Once I kind of got back momentum I just tried to sink my teeth into the set," Keys said of the second set.

Melbourne is where Keys made her Grand Slam breakthrough 12 months ago, and throughout her entire trip back so far, people have been asking her how confident she is about defending a major for the first time.

“The emotions are maybe just, like, a little bit more heightened,” she said. “I think in those tough kind of moments like today, getting down in that second set, just kind of reminding yourself that you have been here before, you figured it out.”

Besides, she told the crowd in her on-court interview, winning the Daphne Akhurst Memorial Cup last year will always remain a permanent highlight.

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“That was such an amazing experience and nobody can take that away from me,” she said. “Whether or not I do repeat it, I still get to keep Daphne at home!”

Keys will next face former No. 1-ranked Karolina Pliskova, who had a 6-4, 6-4 win over Janice Tjen of Indonesia. Pliskova played just three matches last year after recovering from ankle surgery following the 2024 U.S. Open.

Two other highly-ranked U.S. women advanced in the same tough quarter of the draw, with No. 4 Amanda Anisimova fending off doubles champion Katerina Siniakova 6-1, 6-4 in a raucous atmosphere on Margaret Court Arena, and sixth-seeded Jessica Pegula having a 6-0, 6-2 win over McCartney Kessler, her doubles partner.

Anisimova, who has been runner-up at the last two major tournaments, will play fellow American Peyton Stearns.

Pegula will next face Oksana Selekhmeteva, who upset 2025 semifinalist Paula Badosa 6-4, 6-4.

Shelton advances

Eighth-seeded Ben Shelton, a semifinalist here last year, reached the third round with a 6-3, 6-2, 6-2 win over Dane Sweeny, the Australian qualifier who ended the 39-year-old Gael Monfils' farewell trip to Melbourne Park in the first round.

Fifth-seeded Lorenzo Musetti beat fellow Italian Lorenzo Sonego 6-3, 6-3, 6-4.

More on Day 5

Jannik Sinner will continue his bid for a third straight Australian title when he takes on local wild-card entry James Duckworth in the first night match on Rod Laver Arena.

Two-time Australian Open winner Naomi Osaka, who made a grand entrance in her opening match, will take on Sorana Cirstea on Margaret Court Arena.