Stadium: Clay Court 2 Round: 44 Ground: Clay
| ITF - W15 Héraklion | 2019/11/17 07:30 | Fowler, Jessica v Marnellou, Maria | 6-1,6-0 |
| ITF - W15 Héraklion | 2019/11/10 07:30 | Irene Lavino v Fowler, Jessica | 3-6,6-3,10-7 |
| ITF - W15 Héraklion | 2019/11/06 10:10 | Daniela Vismane v Fowler, Jessica | 6-0,4-6,6-3 |
| ITF - W15 Héraklion | 2019/11/05 07:30 | Skorupska, Anastasiya v Fowler, Jessica | 4-6,3-6 |
| ITF - W15 Héraklion | 2019/11/04 08:00 | Fowler, Jessica v Zlatarova, Aleksandra | 2-6,6-1,10-7 |
| ITF W60 Bendigo | 2019/10/20 23:00 | Fowler, Jessica v Laura Ashley | 6-7,3-6 |
| Hua Hin, Simples W-ITF-THA-10A | 2019/10/14 03:00 | Kanako Osafune v Fowler, Jessica | 6-3,6-1 |
| Hua Hin, Simples W-ITF-THA-10A | 2019/10/09 07:50 | Fowler, Jessica v Sawasdee, Watsachol | 5-7,3-6 |
| ITF - W15 Héraklion | 2019/11/10 07:30 | Powaska-Kobylarz, Anna v Novac, Izabela Gabriela | 2-6,2-6 |
| Parnu, Singles Qualifying W-ITF-EST-01A | 2019/11/05 10:30 | Powaska-Kobylarz, Anna v Anna Ozerova | 2-6,2-6 |
| ITF W15 Lousada | 2019/10/23 16:35 | Powaska-Kobylarz, Anna v Orange, Margaux | 1-6,6-3,3-6 |
| ITF W15 Lousada | 2019/10/21 12:00 | Elizabet Hamaliy v Powaska-Kobylarz, Anna | 4-6,0-6 |
| ITF W15 Lousada | 2019/10/20 12:00 | Reis, Carolina Caetano v Powaska-Kobylarz, Anna | 2-6,0-6 |
| ITF W15 Sozopol | 2019/10/02 07:00 | Powaska-Kobylarz, Anna v Oana Gavrila | 4-6,6-4,1-6 |
| ITF W15 Sozopol | 2019/09/30 07:00 | Powaska-Kobylarz, Anna v Aleksandra Julia Zuchanska | 3-6,6-3,10-7 |
| Brno, Singles Qualifying W-ITF-CZE-11A | 2019/09/22 08:00 | Lucie Petruzelova v Powaska-Kobylarz, Anna | 6-4,6-0 |