Djokovic Nears Uncharted Milestone, Wawrinka Shines at 40 in Melbourne

The Australian Open witnessed a historic day on Thursday as Novak Djokovic edged closer to an unprecedented milestone while Stan Wawrinka rewrote age-defying records , underlining Melbourne Park’s reputation as a stage for tennis immortality.

Djokovic cruised past Italian qualifier Francesco Maestrelli 6-3, 6-2, 6-2 to register his 399th Grand Slam match win , moving within one victory of becoming the first player in history to reach 400 wins at majors . The 38-year-old Serbian, already the most decorated men’s singles champion with 24 Grand Slam titles , is also bidding for a record-breaking 25th major crown .

Should Djokovic lift the trophy in Melbourne, he would surpass Ken Rosewall to become the oldest men’s singles champion in the Open Era . Rosewall, whose legacy loomed large at Melbourne Park on Day 5, was among the invited dignitaries in attendance.

Despite being pushed into the afternoon session due to Jannik Sinner’s prime-time night match , Djokovic remained unfazed. Though he dropped his first service game of the tournament in the third set, he responded emphatically, breaking back immediately and finishing the match with authority. Djokovic later said his offseason focus on refining specific aspects of his game was key to sustaining excellence at this stage of his career.

The day’s other standout moment came from Stan Wawrinka , who at 40 years and 310 days became the first man over 40 to reach the third round of a Grand Slam since Rosewall in 1978 . The Swiss veteran staged a gripping 4½-hour comeback to defeat 21-year-old French qualifier Arthur Gea in five sets, the longest match of the tournament so far. Wawrinka, set to retire at the end of the season, will next face ninth seed Taylor Fritz .

Elsewhere, defending champion Jannik Sinner remained firmly on course for an Australian Open hat-trick , dispatching James Duckworth in straight sets. American Ben Shelton advanced comfortably, while notable upsets saw Marin Cilic eliminate Denis Shapovalov and Tomas Machac stun former finalist Stefanos Tsitsipas .

In the women’s draw, Iga Swiatek progressed smoothly and credited Djokovic’s longevity for inspiring her approach to sustained success. Madison Keys , Amanda Anisimova , and Jessica Pegula also moved into the third round.

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