Jacob Fearnley defeated Tomáš Macháč 1–6, 6–3, 6–2 in the first round of the Madrid Masters on clay on 26 April 2025, securing an upset victory against the pre-match favourite. Macháč began dominantly, claiming the opening set with ease, but Fearnley regrouped to take control of the second and third sets, breaking the Czech player's resistance with increasingly commanding tennis. The turnaround proved decisive as Fearnley, the underdog at 3.2 odds, managed the conditions effectively after a sluggish start to progress through the opening round. The result marks a significant scalp for Fearnley at Masters level and suggests improved clay-court form heading deeper into the tournament.