| WTA Tokyo | 09/19 08:00 | 25 | [92] Ozaki, Risa v Shelby Rogers [59] | 2-6,6-7 | |
| WTA Tokyo | 09/12 07:00 | 25 | [90] Ozaki, Risa v Magda Linette [76] | 1-6,5-7 | |
| US Open Women | 08/31 20:35 | 24 | [96] Ozaki, Risa v Shuai Zhang [26] | 0-6,3-6 | |
| US Open Women | 08/30 19:35 | 23 | [96] Ozaki, Risa v Lao, Danielle [219] | 6-3,6-7,7-6 | |
| WTA New Haven Qual | 08/18 19:45 | 44 | [94] Ozaki, Risa v Varvara Lepchenko [65] | 3-6,3-6 | |
| WTA Cincinnati Qual | 08/12 18:40 | 44 | [58] Barty, Ashleigh v Ozaki, Risa [95] | 7-5,6-2 | |
| WTA Toronto Qual | 08/06 16:05 | 45 | [64] Arruabarrena, L. v Ozaki, Risa [78] | 7-5,6-4 | |
| WTA Toronto Qual | 08/05 17:40 | 44 | [265] Robillard-Millette, Charlotte v Ozaki, Risa [78] | 3-6,3-6 | |
| WTA Washington | 07/31 22:50 | 25 | [78] Ozaki, Risa v Sara Errani [103] | 6-7,2-6 | |
| Nanchang, Chine | 07/25 10:40 | 25 | [79] Ozaki, Risa v Lin Zhu [122] | 0-6,5-7 | |
| Wimbledon Women | 07/04 13:40 | 23 | [107] Satralova, Denisa v Ozaki, Risa [77] | 7-6,2-6,6-3 | |
| WTA Eastbourne | 06/26 11:20 | 24 | [58] Naomi Osaka v Ozaki, Risa [75] | 6-0,6-1 | |
| WTA Eastbourne Qual | 06/24 17:50 | 46 | [67] Varvara Lepchenko v Ozaki, Risa [74] | 6-4,6-4 | |
| WTA Eastbourne Qual | 06/23 16:05 | 45 | [216] Cako, Jacqueline v Ozaki, Risa [74] | 5-7,0-6 | |
| WTA Mallorca | 06/20 17:00 | 25 | Ozaki, Risa v Victoria Azarenka | 3-6,6-4,6-7 | |
| WTA Den Bosch | 06/13 16:15 | 25 | [73] Ozaki, Risa v Kristina Mladenovic [13] | 5-7,1-6 | |
| Open de France - Femmes | 05/30 15:00 | 23 | [72] Ozaki, Risa v Eugenie Bouchard [57] | 6-2,3-6,2-6 | |
| WTA - Strasbourg | 05/21 09:00 | 25 | [72] Ozaki, Risa v Qiang Wang [57] | 4-6,6-3,3-6 | |
| WTA Rome Qual | 05/14 12:40 | 46 | [64] Qiang Wang v Ozaki, Risa [71] | 6-2,6-0 | |
| WTA Rome Qual | 05/13 14:15 | 45 | Federica Di Sarra v Ozaki, Risa | 6-4,3-6,3-6 | |
| WTA Madrid Qual | 05/06 11:50 | 46 | [67] Saisai Zheng v Ozaki, Risa [72] | 6-4,6-4 | |
| WTA Madrid Qual | 05/05 14:05 | 45 | [360] Badosa, Paula v Ozaki, Risa [72] | 3-6,6-2,2-6 | |
| WTA Prague Qual | 04/29 14:15 | 45 | [70] Ozaki, Risa v Hradecka, Lucie [168] | 4-6,7-5,2-6 | |
| WTA Stuttgart Qual | 04/22 15:55 | 45 | [305] Katharina Hobgarski v Ozaki, Risa [71] | 3-6,6-3,6-4 | |
| WTA - Miami | 03/27 19:00 | 26 | [1] Angelique Kerber v Ozaki, Risa [87] | 6-2,6-2 | |
| WTA - Miami | 03/26 15:00 | 25 | [47] Goerges, Julia v Ozaki, Risa [87] | 6-7,3-6 | |
| WTA - Miami | 03/25 03:45 | 24 | [87] Ozaki, Risa v Bertens, Kiki [21] | 6-4,4-6,6-1 | |
| WTA - Miami | 03/22 20:50 | 23 | [87] Ozaki, Risa v Louisa Chirico [63] | 3-6,7-5,6-1 | |
| WTA Miami Qual | 03/21 19:20 | 45 | [87] Ozaki, Risa v Boserup, Julia [97] | 7-5,6-0 | |
| WTA Miami Qual | 03/20 20:10 | 44 | [87] Ozaki, Risa v Katie Swan [338] | 6-3,6-3 |