Anna Kalinskaya defeated Amanda Anisimova 7–5, 6–4 in the first round of the Cincinnati Masters on hard court on 11 August 2025, an upset victory against the pre-match favourite. Anisimova, seeded higher in the betting odds at 1.49, was unable to convert her favoured status, while Kalinskaya capitalised on her underdog position at 2.85 to secure a commanding two-set victory. The result marks a significant scalp for Kalinskaya in the early stages of the tournament and suggests momentum heading into the subsequent rounds.