| US Open Women | 09/02 19:45 | - | [44] Kaia Kanepi v Serena Williams [26] | 0-6,6-4,3-6 | |
| US Open Women | 08/31 20:50 | - | [44] Kaia Kanepi v Rebecca Peterson [61] | 6-3,7-6 | |
| US Open Women | 08/29 20:45 | - | [44] Kaia Kanepi v Jil Teichmann [168] | 6-4,6-3 | |
| US Open Women | 08/27 15:00 | - | [1] Simona Halep v Kaia Kanepi [44] | 2-6,4-6 | |
| WTA Cincinnati | 08/15 16:55 | - | [46] Kaia Kanepi v Ashleigh Barty [16] | 5-7,3-6 | |
| WTA Cincinnati | 08/14 17:15 | - | [46] Kaia Kanepi v Varvara Lepchenko [120] | 2-6,6-3,6-1 | |
| WTA Cincinnati Qual | 08/12 14:00 | - | [48] Kaia Kanepi v Zarina Diyas [63] | 6-3,6-3 | |
| WTA Cincinnati Qual | 08/11 17:00 | - | [48] Kaia Kanepi v Sabine Lisicki [230] | 4-6,6-4,6-3 | |
| WTA Moscow | 07/25 08:00 | - | [187] Olga Danilovic v Kaia Kanepi [49] | 7-6,7-5 | |
| WTA Moscow | 07/23 14:30 | - | [136] Vera Zvonareva v Kaia Kanepi [51] | 2-6,2-6 | |
| Wimbledon Women | 07/03 16:55 | - | [102] Sara Sorribes Tormo v Kaia Kanepi [46] | 7-6,6-1 | |
| WTA Eastbourne | 06/26 10:00 | - | [12] Jelena Ostapenko v Kaia Kanepi [44] | 6-3,7-5 | |
| WTA Eastbourne | 06/25 10:00 | - | [44] Kaia Kanepi v Kurumi Nara [101] | 6-2,6-4 | |
| ITF Women Ilkley | 06/22 10:00 | - | [46] Kaia Kanepi v Ekaterina Alexandrova [112] | 6-3,4-6,6-7 | |
| ITF Women Ilkley | 06/21 10:10 | - | [46] Kaia Kanepi v Irina Falconi [137] | 3-6,6-1,6-2 | |
| ITF Women Ilkley | 06/20 14:40 | - | [46] Kaia Kanepi v Maia Lumsden [422] | 6-3,6-2 | |
| ITF Women Brescia | 06/10 14:00 | - | [52] Kaia Kanepi v Martina Trevisan [185] | 6-4,6-3 | |
| ITF Women Brescia | 06/09 14:25 | - | [52] Kaia Kanepi v Anastasia Grymalska [259] | 6-2,6-0 | |
| ITF Women Brescia | 06/08 12:00 | - | [52] Kaia Kanepi v Ekaterine Gorgodze [273] | 6-1,6-1 | |
| ITF Women Brescia | 06/07 14:25 | - | [52] Kaia Kanepi v Elena Rybakina [195] | 6-2,6-2 | |
| ITF Women Brescia | 06/06 16:00 | - | [52] Kaia Kanepi v Georgia Brescia [250] | 6-2,6-3 | |
| French Open Women | 05/28 12:15 | - | [14] Daria Kasatkina v Kaia Kanepi [51] | 6-4,6-1 | |
| WTA Strasbourg | 05/21 09:00 | - | [49] Su-Wei Hsieh v Kaia Kanepi [51] | 2-6,7-5,6-2 | |
| WTA Strasbourg Qual | 05/19 10:30 | - | [59] Kaia Kanepi v Elena Rybakina [221] | 6-2,6-3 | |
| WTA Strasbourg Qual | 05/18 13:50 | - | Kaia Kanepi v Virginie Razzano | 6-1,6-2 | |
| WTA Rome | 05/16 09:00 | - | [10] Sloane Stephens v Kaia Kanepi [59] | 6-0,5-7,6-4 | |
| WTA Rome | 05/14 10:10 | - | [59] Kaia Kanepi v Camilla Rosatello [270] | 6-1,6-2 | |
| WTA Rome Qual | 05/13 09:00 | - | [51] Katerina Siniakova v Kaia Kanepi [60] | 3-6,6-3,3-6 | |
| WTA Rome Qual | 05/12 08:00 | - | [90] Sofia Kenin v Kaia Kanepi [60] | 6-2,2-6,2-6 | |
| WTA Stuttgart Qual | 04/23 11:30 | - | [52] Zarina Diyas v Kaia Kanepi [61] | 6-4,4-6,6-4 |