Stadium: Court 2 Round: 25 Ground: Hardcourt outdoor
| WTA Bastad | 2019/07/08 12:05 | Caijsa W Hennemann v Aleksandra Krunic | 3-6,1-6 |
| ITF W15 Varberg | 2019/05/18 12:00 | Marina Yudanov v Caijsa W Hennemann | 6-0,6-0 |
| ITF W15 Varberg | 2019/05/17 10:10 | Caijsa W Hennemann v Ania Hertel | 6-1,7-6 |
| ITF W15 Varberg | 2019/05/16 08:30 | Julita Saner v Caijsa W Hennemann | 1-6,5-7 |
| ITF W15 Varberg | 2019/05/15 08:30 | Caijsa W Hennemann v Ingrid Vojcinakova | 6-4,6-2 |
| ITF W15 Gothenburg | 2019/05/12 10:00 | Aneta Laboutkova v Caijsa W Hennemann | 2-6,7-6,6-3 |
| ITF W15 Gothenburg | 2019/05/11 09:00 | Alina Silich v Caijsa W Hennemann | 3-6,1-6 |
| ITF W15 Gothenburg | 2019/05/10 08:30 | Astrid Wanja Brune Olsen v Caijsa W Hennemann | 4-6,3-6 |
| ITF W15 Batumi | 2019/08/28 11:15 | Ani Amiraghyan v Vasilisa Aponasenko | 6-4,4-6,6-2 |
| ITF W25 Moscow | 2019/07/22 11:35 | Vasilisa Aponasenko v Daria Soldatova | 4-6,3-6 |
| ITF W15 Tabarka | 2019/07/10 09:50 | Andrea A Farulla Di Palma v Vasilisa Aponasenko | 6-3,6-2 |
| ITF W15 Tabarka | 2019/07/03 14:00 | Vasilisa Aponasenko v Paula Arias Manjon | 0-6,6-4,6-7 |
| ITF W15 Montemor-O-Novo | 2019/05/30 11:20 | Bojana Klincov v Vasilisa Aponasenko | 6-2,3-6,6-3 |
| ITF W15 Montemor-O-Novo | 2019/05/29 16:30 | Vasilisa Aponasenko v Ana Filipa Santos | 4-6,6-4,6-3 |
| ITF W15 Cantanhede | 2019/05/23 11:40 | Vasilisa Aponasenko v Lisa Ponomar | 3-6,0-6 |
| ITF W15 Cantanhede | 2019/05/21 11:00 | Sara Lanca v Vasilisa Aponasenko | 4-6,2-6 |