Filip Krajinovic defeated Daniel Evans 6–3, 6–4 in the first round of the Cincinnati Masters on hard court. Evans, the pre-match favourite at 1.54 odds, was unable to convert his seeding advantage, with Krajinovic at 2.67 odds securing a convincing upset victory. The Serbian player's composed performance across both sets demonstrated control of the rallies and effective serving, allowing him to advance without facing significant resistance. The result marked a notable upset in the opening round, with Krajinovic moving into the second round whilst Evans' campaign at the Masters 1000 event ended prematurely.