Djokovic one away from 400 Grand Slam match wins; Wawrinka makes history

Novak Djokovic of Serbia reacts during his second round match against Francesco Maestrelli of Italy at the Australian Open tennis championship in Melbourne, Australia, Thursday, Jan. 22, 2026. (AP Photo/Aaron Favila)

MELBOURNE, Australia -- Novak Djokovic and Stan Wawrinka made it a day for the ages at the Australian Open.

Djokovic improved to 399 wins in Grand Slam matches with a 6-3, 6-2, 6-2 victory over Francesco Maestrelli on Thursday, making the 38-year-old, 24-time major winner just one shy of becoming the first player ever to 400.

He’s aiming to win an unprecedented 25th Grand Slam title. And if he does, he’ll beat Ken Rosewall’s record (aged 37 in 1972) as the oldest man in the Open era to win a major singles championship.

The Rosewall name was prominent on Day 5 at Melbourne Park, where he was among the invited VIPs.

Wawrinka, at 40 years, 310 days, became the first man over 40 to reach the third round of a major since Rosewall in 1978. It took a 4 1/2-hour 4-6, 6-3, 3-6, 7-5, 7-6 (3) comeback victory over 21-year-old qualifier Arthur Gea. That’s the longest match of the 2026 tournament so far.

Wawrinka, who is retiring at the end of the year, will next face No. 9 Taylor Fritz.

Before then, he told the crowd at John Cain Arena: “I think I’ll pick up a beer. I deserve one!”

His was one of three high-profile matches that finished around the same time, with Jannik Sinner continuing his bid for an Australian Open three-peat after beating James Duckworth 6-1, 6-4, 6-2 on Rod Laver Arena.

The defining feature of Naomi Osaka’s first two rounds quickly moved from fashion to friction when her 6-3, 4-6, 6-2 win over Sorana Cirstea ended in tension.

“I think this was her last Australian Open so, OK, sorry she was mad about it,” Osaka said.

Day and night

With Sinner facing an Australian wild card, he got the prime time night slot and bumped 10-time Australian Open winner Djokovic into the afternoon session.

That didn’t bother Djokovic as much as the dropped service game in the third set -- his first of the tournament. It stung Djokovic, who broke the Italian qualifier at love in the next game and finished on an eight-point roll.

He said he took extra time out in the offseason and fine-tuned some skills as he chases his biggest goals.

“When I have more time, then I obviously try to look at my game and different elements that I can really improve. Otherwise, what’s the point?” he said. “That’s the kind of mentality I try to nurture. It’s been allowing to me play at the highest level at this age.”

Iga Świątek beat Marie Bouzkova 6-2, 6-3 and later said she’s been trying to take lessons from Djokovic’s attitude to sustained success and longevity.

“It’s good to look at people like that and find inspiration,” the six-time major winner said. “For sure I’ve got to learn to appreciate every single match,” she said.

Keys to success

Defending champion Madison Keys was down a double break in the second set before rallying to beat Ashlyn Krueger 6-1, 7-5 and advancing to a third-round match against former No. 1 Karolina Pliškova.

Melbourne is where Keys made her Grand Slam breakthrough 12 months ago and since her return people have been asking her how confident she is about retaining the Daphne Akhurst Memorial Cup.

“Whether or not I do repeat it,” she said, “I still get to keep Daphne at home!”

In that tough quarter of the draw, No. 4 Amanda Anisimova fended off doubles champion Katerina Siniakova 6-1, 6-4 and sixth-seeded Jessica Pegula won 6-0, 6-2 over McCartney Kessler, her doubles partner.

Anisimova, who has been runner-up at the last two major tournaments, will next play fellow American Peyton Stearns. Pegula will next face Oksana Selekhmeteva, who upset 2025 semifinalist Paula Badosa 6-4, 6-4.

No. 5 Elena Rybakina advanced over Varvara Gracheva and No. 10 Belinda Bencic was ousted by Nikola Bartunkova.

Men’s draw

Eighth-seeded Ben Shelton, a semifinalist here last year, reached the third round with a 6-3, 6-2, 6-2 win over Australian qualifier Dane Sweeny.

His fellow American Eliot Spizzirri beat Wu Yibing in five grueling sets and will next face Sinner. Two men’s seeds tumbled: Marin Cilic, the 2014 U.S. Open winner, ousted No. 21 Denis Shapovalov and Tomas Machac upset 2023 Australian Open runner-up Stefanos Tsitsipas 6-4, 3-6, 7-6 (5), 7-6 (5).

Big, big crowds

The combined day and night crowd set a tournament record for the fourth time in five days, rising to 103,720. The cumulative total for the main draw so far is 508,430, prompting a lot of chatter about crowding.

Light will win

Before the start of the night session, spectators were asked to join in a moment of silence to remember the 15 people killed in the Bondi Beach terror attack last month. It was designated a national day of mourning in Australia and signs in Melbourne Park highlighted the message: “Light Will Win.”

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John Pye, The Associated Press