It will be an all-Czech affair when Tomas Machac and Jakub Mensik collide in the Acapulco first round on Monday. This night-only ATP 500 tournament also gets underway with Ben Shelton facing Flavio Cobolli.

Jakub Mensik vs. (8) Tomas Machac

Machac was one of the ATP Tour’s breakout performers in 2024 and he has been just as good so far this season. The 24-year-old Czech is up to 25th in the rankings thanks in part to seven match victories in 2025, including a third-round showing at the Australian Open and a quarterfinal finish in Dallas. Heading into the Abierto Mexicano Telcel, Machac has already spent time in Mexico this month; he won the UTS Guadalajara title a week ago.

Up first for the No. 8 seed on Monday is a first-ever showdown against Mensik, who also played UTS Guadalajara and exited in round-robin action after being under the weather throughout the event. The 19-year-old Czech has also won seven matches this season, highlighted by a third-round effort at the Aussie Open and quarterfinal results in Brisbane and Auckland. Despite his youth, you pretty much know what Mensik will bring to the table every time he takes the court. Machac, on the other hand, can be all over the place despite his immense talent. Moreover, Mensik’s huge-serving game should be particularly effective in the Acapulco conditions.

Pick: Mensik in 3

Flavio Cobolli vs. (5) Ben Shelton

Shelton and Cobolli will be going head-to-head for the third time in their careers when they clash on Monday. Cobolli has won both of their previous encounters; 4-6, 7-6(1), 6-2 on the red clay of Geneva in 2024 and 4-6, 7-5, 6-3 a few months later in the Washington, D.C. semifinals.

Following two very near misses against his fellow On Running ambassador, Shelton should feel good about his chances of turning the tide. The 14th-ranked American reached the semifinals at Melbourne Park and–like Mensik–his power is going to be tough to deal with in Acapulco. As for Cobolli, he appears to be enduring a proverbial “sophomore slump.” The 39th-ranked Italian is 2-5 so far this year and goes into this week on a five-match winning streak. All signs point to Shelton winning this one with relative ease.

Pick: Shelton in 2