Defending champion Casper Ruud is back in action at the Madrid Masters against the often controversial Stefanos Tsitsipas. Daniil Medvedev will also take the court, as he faces Flavio Cobolli.
(12) Casper Ruud vs. Stefanos Tsitsipas
Stefanos Tsitsipas’ ranking is in a free-fall at the moment. The one-time world No. 3 sits at No. 80 right now. He has hardly won more than a match or two at a single event all year — until the Mutua Madrid Open, where he suddenly finds himself in the round of 16.
Unfortunately for the Greek, it’s likely that his best streak of the year is about to come to an end. Casper Ruud has absolutely dismantled his other two opponents this fortnight, including a rout of Alejandro Davidovich Fokina in the third round. Ruud holds a slight 3-2 head-to-head lead over Tsitsipas, but they haven’t played each other since 2024.
Cheryl pick: Ruud in 2
Ricky pick: Ruud in 2
(7) Daniil Medvedev vs. (10) Flavio Cobolli
A couple of weeks ago in Monte-Carlo, Daniil Medvedev got double-bagled by Matteo Berrettini. Let that sink in for a moment. Medvedev is ranked in the top 10 and he failed to win a single game in 12 tries. The point being that there is no way to tell which Medvedev is going to step out on a clay court. It might be the version who won the Rome Masters in 2023, or it might just as easily be the version who let Berrettini win 12 straight games.
Medvedev’s fourth-round opponent, Italy’s Flavio Cobolli, is a good clay-courter who is in fine form. So even if the Russian plays well, he could still be at risk of a loss. Cobolli is in the best form of his career. He won the Acapulco title earlier this spring and made the final last week in Munich. I think Cobolli is going to be hard for Medvedev to beat.
Cheryl pick: Cobolli in 2
Ricky pick: Cobolli in 3