| WTA - Budapest | 02/17 17:05 | 45 | [159] Arina Rodionova v Anna Kalinskaya [144] | 6-0,5-7,6-4 | |
| WTA - Doha | 02/09 10:25 | 45 | [52] Alison Riske v Anna Kalinskaya [144] | 6-2,6-2 | |
| WTA St. Petersburg | 01/28 11:40 | 54 | [146] Anna Kalinskaya v Ekaterina Alexandrova [78] | 6-7,0-6 | |
| WTA St. Petersburg | 01/27 15:05 | 46 | [222] Anastasia Zarycka v Anna Kalinskaya [146] | 4-6,3-6 | |
| WTA St. Petersburg | 01/26 15:55 | 45 | Anna Kalinskaya v Ana Konjuh | 6-4,7-5 | |
| Australian Open - Damen | 01/14 00:00 | 23 | [167] Anna Kalinskaya v Aryna Sabalenka [11] | 1-6,4-6 | |
| Australian Open - Damen | 01/11 03:05 | 46 | [195] Antonia Lottner v Anna Kalinskaya [167] | 6-7,3-6 | |
| Australian Open - Damen | 01/10 06:15 | 45 | [167] Anna Kalinskaya v Vitalia Diatchenko [131] | 6-2,6-2 | |
| Australian Open - Damen | 01/09 02:15 | 44 | [167] Anna Kalinskaya v Quirine Lemoine [227] | 6-1,7-6 | |
| ITF Damen - W25 - Playford | 01/06 03:50 | 29 | [168] Anna Kalinskaya v Elena Rybakina [177] | 6-4,6-4 | |
| ITF Damen - W25 - Playford | 01/05 03:30 | 28 | [225] Chloe Paquet v Anna Kalinskaya [168] | 2-6,4-6 | |
| ITF Damen - W25 - Playford | 01/04 01:55 | 27 | [168] Anna Kalinskaya v Maryna Zanevska [220] | 4-6,6-4,7-6 | |
| ITF Damen - W25 - Playford | 01/03 01:10 | 26 | [168] Anna Kalinskaya v Barbara Haas [219] | 6-3,7-5 | |
| ITF Damen - W25 - Playford | 01/02 01:00 | 25 | Anna Kalinskaya v Ivana Popovic | 6-0,6-4 | |
| ITF Damen - Poitiers | 10/24 10:30 | 26 | [144] Anna Kalinskaya v Arantxa Rus [110] | 3-6,6-3,2-6 | |
| ITF Damen - Poitiers | 10/22 15:30 | 25 | [144] Anna Kalinskaya v Fiona Ferro [100] | 6-2,6-3 | |
| WTA - Moskau | 10/16 11:30 | 25 | [42] Kristina Mladenovic v Anna Kalinskaya [146] | 6-1,6-3 | |
| WTA - Linz | 10/07 17:30 | 45 | [148] Anna Kalinskaya v Natalia Vikhlyan'eva [111] | 1-6,2-6 | |
| WTA - Tashkent | 09/25 06:35 | - | [101] Olga Danilovic v Anna Kalinskaya [144] | 6-4,6-1 | |
| US Open - Damen | 08/27 22:10 | - | [9] Julia Görges v Anna Kalinskaya [143] | 6-2,6-7,6-2 | |
| US Open - Damen | 08/24 20:05 | - | [105] Madison Brengle v Anna Kalinskaya [143] | 3-6,5-7 | |
| US Open - Damen | 08/23 20:10 | - | [144] Mandy Minella v Anna Kalinskaya [143] | 1-6,3-6 | |
| US Open - Damen | 08/22 23:15 | - | [204] Grace Min v Anna Kalinskaya [143] | 2-6,2-6 | |
| ITF Damen - Vancouver | 08/16 19:30 | - | [149] Anna Kalinskaya v Katie Boulter [106] | 5-7,2-6 | |
| ITF Damen - Vancouver | 08/15 17:00 | - | [105] Madison Brengle v Anna Kalinskaya [149] | 3-6,4-6 | |
| WTA - Moskau | 07/24 10:30 | - | [143] Anna Kalinskaya v Daria Kasatkina [13] | 1-6,1-6 | |
| WTA - Gstaad | 07/17 08:30 | - | [186] Elitsa Kostova v Anna Kalinskaya [132] | 6-4,0-6,6-2 | |
| ITF Damen - Contrexeville | 07/14 14:35 | - | [102] Sara Sorribes Tormo v Anna Kalinskaya [146] | 6-4,6-4 | |
| ITF Damen - Contrexeville | 07/13 09:30 | - | [116] Ysaline Bonaventure v Anna Kalinskaya [146] | 6-3,1-6,4-6 | |
| ITF Damen - Contrexeville | 07/12 08:30 | - | [146] Anna Kalinskaya v Kateryna Kozlova [67] | 6-4,7-6 |