Stadium: Court 1 Round: 25 Ground: Clay
| 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 Women Toronto | 2018/10/31 15:20 | Bianca Andreescu v Mari Osaka | 6-1,6-1 |
| ITF Women Florence | 2018/10/21 17:00 | Mari Osaka v Bianca Andreescu | 4-6,6-2,3-6 |
| ITF Women Florence | 2018/10/20 17:55 | Katie Volynets v Mari Osaka | 2-6,6-4,3-6 |
| ITF Women Florence | 2018/10/19 14:00 | Mari Osaka v Paula Cristina Goncalves | 5-7,6-4,6-1 |
| ITF Women Florence | 2018/10/18 14:00 | Ulrikke Eikeri v Mari Osaka | 1-6,3-6 |
| ITF W25 Kazan | 2019/03/17 08:00 | Elena Rybakina v Urszula Radwanska | 6-2,6-3 |
| ITF W25 Kazan | 2019/03/16 09:00 | Lucia Bronzetti v Urszula Radwanska | 5-7,3-6 |
| ITF W25 Kazan | 2019/03/15 09:10 | Urszula Radwanska v Kamilla Rakhimova | 6-7,7-5,6-4 |
| ITF W25 Kazan | 2019/03/14 07:00 | Dalma Galfi v Urszula Radwanska | 6-4,4-6,3-6 |
| ITF W25 Kazan | 2019/03/13 12:05 | Anastasia Tikhonova v Urszula Radwanska | 4-6,2-6 |
| ITF W25 Altenkirchen | 2019/02/20 14:50 | Urszula Radwanska v Susan Bandecchi | 2-6,4-6 |
| ITF W100 Midland | 2019/01/30 15:00 | Madison Brengle v Urszula Radwanska | 7-6,6-3 |
| ITF W100 Midland | 2019/01/29 17:25 | Urszula Radwanska v Emina Bektas | 6-4,6-3 |