Stadium: Stadium (Ct 9) Round: 26 Ground: Clay
| ITF W25 Pelham | 2019/04/10 16:05 | Mari Osaka v Kayla Day | 6-3,6-4 |
| ITF W25 Pelham | 2019/04/09 21:30 | Mari Osaka v Panna Udvardy | 7-6,6-3 |
| ITF W25 Pelham | 2019/04/08 15:00 | Mari Osaka v Epiphany B. Turner | 6-0,6-0 |
| ITF W80 Palm Harbor | 2019/04/04 17:45 | Mari Osaka v Kurumi Nara | 6-7,4-6 |
| ITF W80 Palm Harbor | 2019/04/02 19:25 | Mari Osaka v Urszula Radwanska | 6-1,7-6 |
| WTA Miami | 2019/03/21 16:25 | Whitney Osuigwe v Mari Osaka | 6-2,6-4 |
| ITF W100 Midland | 2019/01/28 20:40 | Emina Bektas v Mari Osaka | 6-1,6-4 |
| WTA Newport Beach | 2019/01/22 18:00 | Mari Osaka v Katie Volynets | 0-6,0-6 |
| ITF W25 Pelham | 2019/04/10 18:30 | Michaela Honcova v Sesil Karatantcheva | 0-6,0-6 |
| WTA Charleston | 2019/03/31 16:40 | Martina Trevisan v Sesil Karatantcheva | 6-2,6-3 |
| WTA Charleston | 2019/03/30 17:50 | Darija Jurak v Sesil Karatantcheva | 2-6,2-6 |
| WTA Indian Wells | 2019/02/25 23:30 | Caty McNally v Sesil Karatantcheva | 5-7,6-4,6-4 |
| ITF W25 Rancho Santa Fe | 2019/02/22 19:50 | Sesil Karatantcheva v Ann Li | 3-6,5-7 |
| ITF W25 Rancho Santa Fe | 2019/02/20 20:35 | Sesil Karatantcheva v Hua-Chen Lee | 6-4,6-7,6-4 |
| ITF W25 Surprise | 2019/02/17 18:00 | Cori Gauff v Sesil Karatantcheva | 7-5,3-6,1-6 |
| ITF W25 Surprise | 2019/02/16 18:00 | Sesil Karatantcheva v Allie Kiick | 6-1,6-3 |