Stadium: Stadium (Ct 9) Round: 25 Ground: Clay
| ITF W80 Palm Harbor | 2019/04/02 19:25 | Mari Osaka v Urszula Radwańska | 6-1,7-6 |
| ITF - Kazan W25 | 2019/03/17 08:00 | Elena Rybakina v Urszula Radwańska | 6-2,6-3 |
| ITF - Kazan W25 | 2019/03/16 09:00 | Lucia Bronzetti v Urszula Radwańska | 5-7,3-6 |
| ITF - Kazan W25 | 2019/03/15 09:10 | Urszula Radwańska v Kamilla Rakhimova | 6-7,7-5,6-4 |
| ITF - Kazan W25 | 2019/03/14 07:00 | Dalma Galfi v Urszula Radwańska | 6-4,4-6,3-6 |
| ITF - Kazan W25 | 2019/03/13 12:05 | Anastasia Tikhonova v Urszula Radwańska | 4-6,2-6 |
| ITF - Altenkirchen W25 | 2019/02/20 14:50 | Urszula Radwańska v Susan Bandecchi | 2-6,4-6 |
| ITF - Midland W100 | 2019/01/30 15:00 | Madison Brengle v Urszula Radwańska | 7-6,6-3 |
| WTA Charleston | 2019/03/31 14:30 | Caroline Dolehide v Nadiia Kichenok | 6-7,6-4,6-7 |
| WTA Charleston | 2019/03/30 16:00 | Caroline Dolehide v Lidziya Marozava | 6-2,6-3 |
| WTA Miami | 2019/03/18 18:10 | Caroline Dolehide v Magda Linette | 5-7,6-7 |
| WTA Indian Wells | 2019/03/04 23:15 | Stefanie Voegele v Caroline Dolehide | 6-2,3-6,6-3 |
| WTA Indian Wells | 2019/02/25 21:05 | Olga Danilovic v Caroline Dolehide | 4-6,6-3,6-1 |
| ITF - Rancho Santa Fe W25 | 2019/02/20 18:00 | Caroline Dolehide v Gabriela Ce | 6-7,5-7 |
| ITF - Rancho Santa Fe W25 | 2019/02/19 18:00 | Caroline Dolehide v Haley Giavara | 6-1,6-2 |
| ITF - Rancho Santa Fe W25 | 2019/02/18 21:00 | Caroline Dolehide v Sabastiani Leon | 6-2,6-2 |