Anna Kalinskaya and Mccartney Kessler have met 1 time; Kalinskaya leads 1–0. Most recently Kalinskaya won 6-2, 6-7(3), 6-4 in the second round at National Bank Open - Toronto on August 4, 2026. By surface: hard 1–0. Kalinskaya is ranked No. 21, Kessler No. 72.

Every meeting

From the match records held by our data provider, main tour, Challenger and ITF levels included. Walkovers are not counted as meetings.