| ITF Damen - Poitiers | 10/22 15:30 | - | [144] Anna Kalinskaya v Fiona Ferro [100] | 6-2,6-3 | |
| WTA - Moskau | 10/16 11:30 | - | [42] Kristina Mladenovic v Anna Kalinskaya [146] | 6-1,6-3 | |
| WTA - Linz | 10/07 17:30 | - | [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 | |
| ITF Damen - Contrexeville | 07/11 08:00 | - | [326] Sara Cakarevic v Anna Kalinskaya [146] | 3-6,1-6 | |
| Wimbledon - Damen - Quaifikation | 06/28 10:00 | - | [146] Anna Kalinskaya v Viktoriya Tomova [136] | 4-6,7-6,3-6 | |
| Wimbledon - Damen - Quaifikation | 06/27 10:00 | - | [92] Dalila Jakupovic v Anna Kalinskaya [146] | 2-6,6-7 | |
| Wimbledon - Damen - Quaifikation | 06/26 12:40 | - | [185] Sabine Lisicki v Anna Kalinskaya [146] | 4-6,6-7 | |
| ITF Damen - Ilkley | 06/21 10:00 | - | [190] Harriet Dart v Anna Kalinskaya [147] | 6-4,6-1 | |
| ITF Damen - Ilkley | 06/20 13:15 | - | [147] Anna Kalinskaya v Arantxa Rus [106] | 6-0,6-4 | |
| WTA - Hertogenbosch | 06/12 12:15 | - | [142] Anna Kalinskaya v Kirsten Flipkens [60] | 3-6,0-6 | |
| French Open - Damen - Qualifikation | 05/25 09:50 | - | [110] Viktorija Golubic v Anna Kalinskaya [158] | 3-6,7-6,6-4 | |
| French Open - Damen - Qualifikation | 05/24 09:30 | - | [158] Anna Kalinskaya v Valentini Grammatikopoulou [176] | 3-6,6-1,6-2 | |
| French Open - Damen - Qualifikation | 05/22 13:25 | - | [158] Anna Kalinskaya v Kayla Day [192] | 6-2,6-0 | |
| WTA - Prag - Qualifikation | 04/28 12:30 | - | Anastasia Zarytska v Anna Kalinskaya | Retired | |
| WTA - Istanbul | 04/24 10:55 | - | [121] Danka Kovinic v Anna Kalinskaya [145] | 6-3,6-3 | |
| WTA - Istanbul - Qualifikation | 04/23 08:00 | - | [132] Sara Sorribes Tormo v Anna Kalinskaya [145] | 3-6,7-5,3-6 | |
| WTA - Istanbul - Qualifikation | 04/22 08:00 | - | Ena Kajevic v Anna Kalinskaya | 4-6,4-6 | |
| ITF Damen - Croissy-Beaubourg | 03/30 17:00 | - | [240] Karolina Muchova v Anna Kalinskaya [156] | 6-1,4-6,6-3 |