| WTA Stuttgart Qual | 04/23 11:30 | - | [52] Zarina Diyas v Kaia Kanepi [61] | 6-4,4-6,6-4 | |
| WTA Stuttgart Qual | 04/22 14:15 | - | [161] Dayana Yastremska v Kaia Kanepi [62] | 2-6,4-6 | |
| WTA Stuttgart Qual | 04/21 18:05 | - | [275] Chloe Paquet v Kaia Kanepi [62] | 2-6,1-6 | |
| WTA Miami | 03/20 16:00 | - | [91] Christina McHale v Kaia Kanepi [59] | Retired | |
| WTA Indian Wells | 03/09 22:35 | - | Coco Vandeweghe v Kaia Kanepi | 6-0,7-6 | |
| WTA Indian Wells | 03/08 00:05 | - | Kurumi Nara v Kaia Kanepi | 6-1,4-6,4-6 | |
| Australian Open Women | 01/19 07:20 | - | Kaia Kanepi v Carla Suarez Navarro | 6-3,1-6,3-6 | |
| Australian Open Women | 01/17 07:00 | - | Kaia Kanepi v Monica Puig | 6-4,6-3 | |
| Australian Open Women | 01/15 01:30 | - | Dominika Cibulkova v Kaia Kanepi | 2-6,2-6 | |
| WTA Brisbane | 01/04 09:00 | - | Kaia Kanepi v Karolina Pliskova | 6-3,5-7,2-6 | |
| WTA Brisbane | 01/03 05:00 | - | Lesia Tsurenko v Kaia Kanepi | 4-6,3-6 | |
| WTA Brisbane | 01/01 01:00 | - | Kaia Kanepi v Daria Kasatkina | 6-2,6-2 | |
| WTA Brisbane Qual | 12/31 02:00 | - | Heather Watson v Kaia Kanepi | 4-6,1-6 | |
| WTA Brisbane Qual | 12/30 03:15 | - | Sara Tomic v Kaia Kanepi | 1-6,4-6 | |
| WTA Brisbane Qual | 12/29 01:30 | - | Kimberly Birrell v Kaia Kanepi | 1-6,3-6 | |
| WTA Limoges | 11/10 15:10 | - | [91] Pauline Parmentier v Kaia Kanepi [107] | 6-2,6-4 | |
| WTA Limoges | 11/09 19:00 | - | [269] Jessika Ponchet v Kaia Kanepi [107] | 1-6,2-6 | |
| WTA Limoges | 11/08 16:25 | - | [147] Maryna Zanevska v Kaia Kanepi [107] | 1-6,3-6 | |
| ITF Women Nantes | 11/05 13:30 | - | [106] Kaia Kanepi v Richel Hogenkamp [110] | 6-3,6-4 | |
| ITF Women Nantes | 11/04 15:10 | - | [106] Kaia Kanepi v Bernarda Pera [127] | 4-6,6-4,6-1 | |
| ITF Women Nantes | 11/03 15:45 | - | [106] Kaia Kanepi v Anna Blinkova [135] | 2-6,6-2,6-4 | |
| ITF Women Nantes | 11/01 15:10 | - | [106] Kaia Kanepi v Mari Osaka [297] | 2-6,7-6,6-0 | |
| ITF Women Nantes | 10/31 14:25 | - | [106] Kaia Kanepi v Sherazad Reix [259] | 6-1,7-6 | |
| WTA Moscow | 10/17 09:55 | - | Natalia Vikhlyantseva v Kaia Kanepi | 6-3,6-2 | |
| WTA Moscow Qual | 10/16 10:40 | - | [109] Kaia Kanepi v Alisa Kleybanova [387] | 6-2,2-6,7-6 | |
| WTA Moscow Qual | 10/15 12:35 | - | [110] Kaia Kanepi v Ivana Jorovic [194] | 6-2,6-0 | |
| WTA Moscow Qual | 10/14 15:30 | - | [110] Kaia Kanepi v Olga Ianchuk [261] | 6-2,6-1 | |
| US Open Women | 09/06 23:00 | - | [16] Madison Keys v Kaia Kanepi [418] | 6-3,6-3 | |
| US Open Women | 09/04 19:00 | - | [38] Daria Kasatkina v Kaia Kanepi [418] | 4-6,4-6 | |
| US Open Women | 09/02 16:30 | - | [418] Kaia Kanepi v Naomi Osaka [45] | 6-3,2-6,7-5 |