The ATP 500 in Doha will begin with a bang on Monday, when top seed Carlos Alcaraz gets his week started against Marin Cilic. Meanwhile, a blockbuster first-round matchup features Grigor Dimitrov and Jiri Lehecka.

(1) Carlos Alcaraz vs. (PR) Marin Cilic

Alcaraz and Cilic 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 Qatar ExxonMobil Open on Monday. A U.S. Open fourth-round thriller three years ago went Alcaraz’s way via a 6-4, 3-6, 6-4, 4-6, 6-3 decision, giving him a 3-1 advantage in the head-to-head series. Cilic’s lone victory came in their first-ever encounter–a 6-3, 1-6, 6-4 result on the red clay of Estoril in 2021.

Fast forward to 2025 and Cilic is undoubtedly in the twilight of his career at 36 years old. The oft-injured Croat finds himself down at No. 195 in the world and he has not yet played a match this season due to a recurring knee problem. Having face Alcaraz right off the bat certainly adds insult to injury. The third-ranked Spaniard boasts a 9-1 record so far in 2025 and is coming off a title in Rotterdam, so he has plenty of momentum heading into Doha. This should be one-way traffic from start to finish.

Pick: Alcaraz in 2

Jiri Lehecka vs. (7) Grigor Dimitrov

The head-to-head rivalry is a similar story in the case of Dimitrov and Lehecka, with the talented youngster leading the veteran 3-1 after losing their first matchup. Dimitrov prevailed 6-4, 4-6, 6-3, 7-5 at the 2022 Australian Open before dropping three in a row, with Lehecka most recently advancing by retirement last month in Brisbane (the 23-year-old led 6-4, 4-4 when it ended).

In fact, Dimitrov has not yet completed a tournament in 2025. After retiring against Lehecka in Brisbane because of a groin injury, the 33-year-old Bulgarian retired from his opening match at Melbourne Park due to a hip issue. He has not played since, so Lehecka has to like his chances on Monday. The Czech has endured recent injury problems of his own, but he is sporting a 10-2 record this year with a title in Brisbane and a fourth-round performance in Melbourne.

Pick: Lehecka in 2