
Several all-seeded showdowns are on the schedule as third-round action in Madrid continues on Monday. Tommy Paul is going up against Karen Khachanov, while Alex de Minaur faces Denis Shapovalov.
(24) Karen Khachanov vs. (11) Tommy Paul
Paul got the draw that no seeded player wants to have in his opening match at any tournament—Joao Fonseca. As expected, it wasn’t easy. In fact, Paul was down set points in each of the two sets but managed to battle past Fonseca 7-6(7), 7-6(3) on Saturday at the Mutua Madrid Open. The 12th-ranked American is now 16-6 this season, which includes a quarterfinal run at the Australian Open and three semifinal appearances.
Up next for Paul on Monday is a second meeting with Khachanov, who lost their only previous encounter in a third-set tiebreaker at the 2022 Miami Masters. Khachanov did well to defeat Reilly Opelka 7-6(3), 7-6(4) on Saturday, but he is still a disappointing 9-9 for the year. Although the 25th-ranked Russian is by no means a bad clay-court player, he does not defend particularly well and he will have to play a lot of long rallies against an opponent who has become an absolute surgeon on the tennis court.
Pick: Paul in 3
(6) Alex de Minaur vs. (29) Denis Shapovalov
De Minaur and Shapovalov will be squaring off for the sixth time in their careers on Monday. The head-to-head series stands at 4-1 in favor of De Minaur, who is 4-0 against Shapovalov on the main tour (the Canadian’s lone win came in 2017 during qualifying at the Surbiton Challenger). They have not faced each other since 2022 (De Minaur won in straight sets in both Montreal and Stockholm) and they have never met on clay.
Although the seventh-ranked Australian has never been at his best on clay, he is balling on every surface these days. De Minaur is 23-8 in 2025 after erasing Lorenzo Sonego 6-2, 6-3 on Saturday, and his clay-court swing already features a semifinal showing in Monte-Carlo and a quarterfinal performance in Barcelona. Shapovalov was 0-2 on clay this spring before beating Kei Nishikori 6-1, 6-4 in the Madrid second round. The left-hander is obviously dangerous, but his high-risk game is especially prone to going off the rails at high altitude, and it will be hard for him to stay patient against an opponent of De Minaur’s defensive caliber.
Pick: De Minaur in 2