Daniil Medvedev has a blockbuster first-round matchup on his hands in Rotterdam, where he will face Stan Wawrinka on Monday. Another intriguing first-rounder features Hubert Hurkacz and Flavio Cobolli.

(WC) Stan Wawrinka vs. (2) Daniil Medvedev

Medvedev and Wawrinka will be squaring off for the fifth time in their careers and for the first time since 2022 when they clash in round one of the ABN AMRO Open on Monday night. The head-to-head series is tied 2-2, with Wawrinka leading 1-0 on indoor hard courts after prevailing 6-4, 6-7(7), 6-3 three years ago in Metz.

At 39 years old, Wawrinka is struggling down at No. 154 in the world–which is why he required a wild card for entry into Rotterdam. The Swiss compiled a 10-17 record on the main tour in 2024 and he is 0-2 this season with losses to Lorenzo Sonego (Australian Open) and Arthur Cazaux (Montpellier). A matchup with Medvedev doesn’t make things any easier–even though Medvedev is far from peak form, himself. The seventh-ranked Russian is looking to bounce back from a shocking five-set setback against Learner Tien in round two of the Aussie Open. On the bright side for Medvedev, he is 10-4 all time in Rotterdam and was the champion in his most recent appearance (2023, d. Jannik Sinner).

Pick: Medvedev in 2

Flavio Cobolli vs. (8) Hubert Hurkacz

Both Hurkacz and Cobolli could really use a productive week in Rotterdam. Hurkacz is 3-4 so far in 2025 and coming off a terrible 6-4, 6-4, 6-2 loss to Miomir Kecmanovic in round two of the Australian Open. Cobolli is 2-4 and in the midst of a four-match losing streak dating back to the United Cup, most recently falling right away in Montpellier to Jesper de Jong in straight sets.

Between these two struggling players, there is a lot more to like about Hurkacz. The 21st-ranked Pole has won 63 matches on indoor hard courts throughout his career, whereas Cobolli is 14-25 lifetime on this surface. Moreover, Hurkacz has won both of their previous head-to-head meetings (7-5, 7-6(2) last summer in Halle and 6-3, 3-6, 6-1 a couple of months later in Cincinnati). If the No. 8 seed’s serve is working on Monday, he should have way too much game for the Italian.

Pick: Hurkacz in 2