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Jannik Sinner vs. Benjamin Bonzi

It’s not often that a player has a chance to break a record held by both Novak Djokovic and Rafael Nadal. But Sinner is approaching that summit in Madrid.

After rolling through the Paris Masters last November, and then Indian Wells, Miami, and Monte Carlo this spring, he’s trying to become the first man to win five straight Masters 1000s since the format was introduced in 1990. Djokovic won four straight on three different occasions, and Nadal did it once. Whatever happens to Sinner in the Magic Box, it’s an early sign that he’s destined to keep some elite historical company.

👉 Stream live on the Tennis Channel app! (Approx. start time 10:00AM ET)

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He’ll start his quest against the 29-year-old Bonzi. His last name makes him sound like a countryman of Sinner’s, but he’s actually from France. He’s ranked 104th and has been as high as 42. He’s best known for beating Daniil Medvedev in the first round at both Wimbledon and the US Open last year. That may not sound all that daunting, but he has always seemed like a more talented ball-striker to me than his results have shown.

Bonzi has flashed some of that talent in his three previous matches with Sinner. While he lost all three, he pushed two of them to a deciding set. All of them came before Sinner rose to No. 1 in the world, so taking another set will be a tougher ask this time, especially in Madrid’s fairly fast conditions. Sinner has never gone deep at this tournament; unfortunately for Bonzi, that will likely make him more motivated to do it this time. Winner: Sinner

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Coco Gauff vs. Leolia Jeanjean

We’ve heard a lot about Iga Swiatek this clay season. We’ve seen Elena Rybakina make an impressive title march in Stuttgart. We’re anticipating Aryna Sabalenka’s return. But what about the defending Roland Garros champ?

She’s been pretty quiet so far. Gauff won a match in Stuttgart last week, then saw her perfect record against Karolina Muchova come to an end. Now the rubber hits the road. Or the sneaker hits the clay.

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Over the next seven weeks, Gauff will be defending finalist’s points in Madrid and Rome, and champion’s points in Paris. She found her A game during the clay swing last year; to keep her No. 3 ranking, she’ll have to do it again. Her run to the final in Miami, where she played something close to her best, was a good sign.

Gauff will begin against Jeanjean, a 30-year-old Frenchwoman with a career-high ranking of 91. They’ve played once before, at the US Open in 2022, and Gauff won 6-2, 6-3. Jeanjean had a couple of decent wins in qualifying, over Vekic and Masarova. But unless Gauff’s serve goes sideways again, she’ll have too much pace and speed for her. Winner: Gauff

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Alex de Minaur vs. Rafael Jodar

For the second time in three nights, a 19-year-old rookie gets the prime evening slot in the Caja Magica. Not that anyone should complain. Jodar is a native Madrileño, and he’s the talk of tennis at the moment. He’s also facing the fifth seed.

The Spaniard and the Australian have yet to play, but we can guess that they’ll give us a classic attacker vs. defender dynamic. Jodar, like many a young player, loves to pulverize any ball that comes his way, and he has the weapons to do it. His flat, skidding backhand in particular has been taking his more experienced opponents by surprise. He’s won nine of his last 10 matches, and a won a title and made a semi already this month. At 6’3, he’ll have three inches, and a fair amount of pace, on De Minaur.

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Can he turn those natural advantages into a victory? De Minaur is an expert defender and competitor, but he hasn’t been great lately; since winning a title in Rotterdam in February, he’s just 4-5. He’s also just 6-6 in Madrid, and has never made a quarterfinal. Jodar will get his looks against him.

All of that said, I think the dogged De Minaur has the experience to weather the crowd, and any early Jodar storm, and find his way to a win. Winner: De Minaur