It’s a tough start to the Wimbledon Championships for Casper Ruud, who goes up against 2021 semifinalist Hubert Hurkacz on Monday. Daniil Medvedev is also in action — and also has a difficult draw — against 2017 finalist Marin Cilic.
(8) Daniil Medvedev vs. Marin Cilic
We don’t have to guess much about this Wimbledon first-round showdown, because these two just did it two weeks ago in ‘s-Hertogenbosch, where Daniil Medvedev came through 6-2, 3-6, 6-1. He owns the head-to-head series 4-1 and has never lost to Marin Cilic on grass. It’s notable that Cilic was ranked 245th in the world two years ago and has clawed his way back to No. 47. He was a finalist at the All-England Club back in 2017; he knows how to play on grass, for sure.
The asterisk is form. Cilic is sitting at 13-13 for the season and lost in the first round at Queen’s Club to Ugo Humbert. Medvedev isn’t exactly arriving white hot, either, after Daniel Altmaier bounced him in the Halle quarterfinals. The Russian has never posted consistent results on grass. He crashed out of Wimbledon right away last year to Benjamin Bonzi — this after reaching the final in Halle, although he reached the semis of Wimbledon two years before that. I’m going to give the nod to Medvedev because he tends to play well against Cilic — but if the Croat won, it certainly wouldn’t be a big upset.
Cheryl pick: Medvedev in 4
Ricky pick: Cilic in 5
(11) Casper Ruud vs. Hubert Hurkacz
Grass is demonstrably Casper Ruud’s worst surface. He’s 5-7 on it for his career, and he has never been past the second round at Wimbledon in five attempts. He shows up this year with no grass-court matches under his belt and roughly a month off since he last competed. Hubert Hurkacz, by contrast, lives for this fortnight. He made the semifinals here in 2021 (with Roger Federer among his victims), he boasts 29 career grass-court wins, and he already has three matches on the surface this year — including a win over Andrey Rublev.


The 2-1 head-to-head edge Ruud holds is a mirage, since none of the meetings were on grass. On a low-bouncing, fast lawn, Hurkacz’s serve (which has been clocked up to 151 mph) and that quick one-two punch are tailor made — while Ruud’s patient baseline grind is largely ineffective. Ruud has made no secret of the fact that he doesn’t much like playing on grass and seems to come into this event each year with no expectations. Hurkacz for the win — and it won’t be an upset, either.
Cheryl pick: Hurkacz in 3
Ricky pick: Hurkacz in 3
