Novak Djokovic Took Maria Sharapova on Dinner Date as a Bet After Winning Match

In a twist that feels straight out of a tennis rom-com, Novak Djokovic once scored a dinner date with Maria Sharapova—not through smooth talking or celebrity connections, but through something far more on-brand: winning a bet on court.

The story resurfaced recently during a playful Q&A session, when Djokovic cheekily recalled a lighthearted wager with the Russian tennis queen. The deal? If Novak could beat her in a challenge—likely involving serves, trick shots, or good old-fashioned competitiveness—Sharapova would have to take him out to dinner. Long story short: Djokovic won, and Sharapova paid up.

While the date didn’t lead to tennis’ next power couple (relax, fans), the story offers a rare glimpse behind the curtain of two of the sport’s most iconic figures. At the time, both were at the peak of their powers—Sharapova with her Grand Slam glam and icy focus, Djokovic with his relentless drive and signature splits. But underneath the trophies and on-court intensity? Just two athletes having fun and teasing each other like schoolyard rivals.

Fans have long speculated about the chemistry between the two. They trained at similar academies, came up through the same tennis circles, and were often spotted joking around during press events. And while nothing romantic ever bloomed, that dinner date has lived on in tennis lore—a little moment that proves even legends like Novak and Maria aren’t above a good-natured bet.

Of course, it’s also peak Djokovic. The man has built a career on outplaying opponents in high-stakes scenarios, so it’s only fitting he’d treat a bet with Sharapova like a Grand Slam final. Charming and competitive? Classic Nole.

Sharapova, for her part, took it in stride. Always poised, she played along with the wager—and even acknowledged Novak’s win with her signature smirk. Whether it was sushi, steak, or something more private, the details of the actual dinner remain a mystery. But one thing’s for sure: fans would’ve paid pay-per-view prices just to witness that exchange of banter over dessert.

In the ever-serious world of professional tennis, it’s refreshing to hear stories like this—where rivalry meets flirtation, and competition turns into camaraderie. And if Djokovic ever makes another bet like that, opponents might want to think twice. He’s not just playing for trophies anymore. Sometimes, he’s playing for dinner with icons.