The only five players in the Rolex Monte-Carlo Masters singles draw who have yet to open their campaigns will do so on Wednesday as the second round comes to a close in Monaco.

Sixth seed Holger Rune meets the resurgent Dominic Thiem in the Monaco evening showpiece, while eighth seed Taylor Fritz starts his clay-court swing against Stan Wawrinka. Third seed Daniil Medvedev will look to continue his red-hot run on a new surface against Lorenzo Sonego, while Casper Ruud seeks to back up his Estoril title run in his opening match against Botic van de Zandschulp. Seventh seed Jannik Sinner rounds out the openers with his matchup against Diego Schwartzman.

ATPTour.com breaks down the biggest matches from the Day 4 slate in the Principality. Only 16 singles competitors will remain at the conclusion of play.

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[6] Holger Rune (DEN) vs. [WC] Dominic Thiem (AUT)

Rune has reached two semi-finals this season, in Montpellier and Acapulco, consolidating his place in the Top 10 of the Pepperstone ATP Rankings. But after his breakthrough title run at the Rolex Paris Masters last November, which lifted him into the Top 10 for the first time, the Dane went 3-2 at the first two ATP Masters 1000s of this season in Indian Wells and Miami.

Now back in action at that prestigious level, the 19-year-old faces another tough test. There was no shame in his defeats to Wawrinka and Fritz at the past two events, but he will be eager to avoid another early exit on the red clay of Monte-Carlo against Thiem.

The Austrian ended a five-match losing streak with a quarter-final run in Estoril last week, and he carried that form into Monte-Carlo, where he earned his first Masters 1000 win since last year in Rome with a 6-1, 6-4 victory against Richard Gasquet. 

“It is important to get matches and you only get them if you win, so last week was a very good step with the quarter-finals,” Thiem said after playing perhaps his best match of 2023. “Here [it] is very nice to win a match, and it is my first win at an [ATP Masters] 1000 tournament for a long time.”

Tuesday’s meeting on Court Rainier III will be the pair’s first ATP Head2Head matchup.

[8] Taylor Fritz (USA) vs. Stan Wawrinka (SUI)

Fritz’s recent rise to the Top 5 of the Pepperstone ATP Rankings was largely built on hard-court success. The 2022 BNP Paribas Open champion stands at World No. 10 entering Monte-Carlo after quarter-final runs at both Indian Wells and Miami, with eight of his 10 ATP Tour finals coming on hard courts and the other two on grass (Eastbourne titles in 2019 and 2022).

Having established himself among the ATP Tour’s elite over the past year, aided by a semi-final run in his Nitto ATP Finals debut, Fritz will now seek to make his mark on clay.

Wawrinka, his opening opponent in Monte-Carlo, believes the Netflix Break Point star is more than capable of continued success on the dirt.

“He is an amazing player,” the Swiss said of Fritz. “He is Top 10, been winning a lot of matches, winning a lot of tournaments. He is very dangerous on many surfaces.”

A champion in Monte-Carlo in 2014, and at Roland Garros one year later, Wawrinka has a long history of clay success. He won the first of his 16 tour-level titles on the clay of Umag in 2006 and owns seven titles on the surface.

The 38-year-old used every bit of his experience to earn a comeback 5-7, 6-3, 6-4 opening win against Tallon Griekspoor on Monday in Monte-Carlo. If he can find a way past Fritz on Court des Princes, it would mark the fourth straight event in which he has recorded at least two victories following a five-set defeat to Alex Molcan in the Australian Open first round.

[3] Daniil Medvedev vs. Lorenzo Sonego (ITA)

Medvedev makes no secret of the fact that clay is not his favourite surface. But the 27-year-old is prepared to adapt his game to the slower conditions as he seeks to maintain the momentum of a scorching stretch that has seen him reach five straight finals and win four titles, culminating with his maiden Miami triumph.

“I definitely have to change my game because my strokes are too flat and clay does not let the ball go through the court as much,” Medvedev said in his pre-tournament press conference. “My opponents can use those [shots against me].

“At the same time, you can’t change what you do in nine months or a year drastically, so I have to find a good balance where I still play my game, with a little change, with some shots in the right moment.”

Sonego, his opening opponent, has proven his ability on all surfaces, with his three ATP Tour titles split between grass, clay and hard courts. The Italian gave Medvedev all he could handle earlier this season in Adelaide in what was the first match of 2023 for both men. In what was their lone previous ATP Head2Head meeting, Medvedev saved nine set points to steal the opener, with Sonego ultimately retiring in the second set due to leg cramps.

Fatigue could be a factor again on Wedneday as Sonego enters their Monte-Carlo meeting without a rest day following his 3-6, 7-5, 7-5 win against Ugo Humbert, during which he saved a match point in stunning fashion.

Also In Action…

In addition to Rune vs. Thiem and Medvedev vs. Sonego, two more marquee matchups are set for Court Rainier III on Wednesday.

Fourth seed Ruud will open the day’s play on the stadium court against van de Zandschulp. The 2022 Roland Garros finalist has won the past two clay events he’s played, in Gstaad last July and in Estoril last week, giving him an eight-match winning streak on his best surface.

Following that, seventh seed Jannik Sinner takes on Diego Schwartzman. The opponents were on the same side of the net in Monte-Carlo doubles action, scoring an opening win before a second-round defeat. Sinner will look to build on semi-final and final runs in Indian Wells and Miami, respectively, while Schwartzman aims to kickstart his 2023 campaign by backing up his opening win against David Goffin.

In Wednesday’s doubles action, top seeds Wesley Koolhof and Neal Skupski meet singles stars Karen Khachanov and Andrey Rublev, while Petros Tsitsipas and Stefanos Tsitsipas look to continue their run against third seeds Marcelo Arevalo and Jean-Julien Rojer.