| ITF W15 Alkmaar | 07/01 10:00 | 28 | Caijsa W Hennemann v Nicole Khirin | 6-4,6-3 | |
| ITF W15 Alkmaar | 06/30 11:30 | 27 | Caijsa W Hennemann v Ariana Geerlings | 6-4,6-4 | |
| ITF W15 Alkmaar | 06/29 14:45 | 26 | Caijsa W Hennemann v Jantje Tilbuerger | 6-2,6-4 | |
| ITF W15 Alkmaar | 06/28 09:00 | 25 | [361] Caijsa W Hennemann v Naima Karamoko [360] | 6-0,6-2 | |
| ITF W40 Ystad | 06/22 12:55 | 26 | [98] Kaia Kanepi v Caijsa W Hennemann [368] | 6-4,6-2 | |
| ITF W40 Ystad | 06/21 10:20 | 25 | Julia Lovqvist v Caijsa W Hennemann | 1-6,1-6 | |
| Billie Jean King Cup | 04/14 07:00 | 1 | [412] Mia Ristic v Caijsa W Hennemann [333] | 6-4,5-7,1-6 | |
| Billie Jean King Cup | 04/13 06:50 | 1 | [333] Caijsa W Hennemann v Petra Marcinko [211] | 6-4,7-5 | |
| Billie Jean King Cup | 04/12 09:00 | 2 | Caijsa W Hennemann v Gergana Topalova | 6-1,5-7,3-6 | |
| Billie Jean King Cup | 04/11 08:00 | 1 | Caijsa W Hennemann v Rebecca Munk Mortensen | 2-6,6-1,6-2 | |
| Billie Jean King Cup | 04/10 08:30 | 1 | Caijsa W Hennemann v Ulrikke Eikeri | 4-6,7-5,6-4 | |
| ITF W25 Santa Margherita | 04/05 12:35 | 25 | [333] Caijsa W Hennemann v Fiona Ferro [434] | 3-6,2-6 | |
| ITF W25 Palmanova | 03/21 07:55 | 62 | [334] Caijsa W Hennemann v Yeonwoo Ku [411] | 6-7,3-6 | |
| ITF W25 Palmanova | 03/20 10:30 | 62 | Caijsa W Hennemann v Martha Matoula | 7-6,7-6 | |
| ITF W25 Palmanova | 03/18 09:00 | 62 | Caijsa W Hennemann v Anastasiya Konstantinovna Soboleva | 4-6,6-2,10-8 | |
| ITF W25 Palmanova | 03/16 12:15 | 26 | [226] Iryna Shymanovich v Caijsa W Hennemann [342] | 6-7,7-5,7-5 | |
| ITF W25 Palmanova | 03/15 08:00 | 25 | [342] Caijsa W Hennemann v Francisca Jorge [298] | 2-6,6-2,6-2 | |
| ITF W15 Amiens | 03/12 13:30 | 29 | Caijsa W Hennemann v Vicky Van De Peer | 6-3,6-1 | |
| ITF W15 Amiens | 03/11 13:55 | 28 | Caijsa W Hennemann v Zongyu Li | 6-2,6-3 | |
| ITF W15 Amiens | 03/10 16:10 | 27 | Caijsa W Hennemann v Maneva Rakotomalala | 6-2,6-1 | |
| ITF W15 Amiens | 03/09 10:00 | 26 | Caijsa W Hennemann v Adriana Rajkovic | Retired | |
| ITF W15 Amiens | 03/08 09:30 | 25 | Caijsa W Hennemann v Veronika Podrez | 7-6,6-4 | |
| ITF W15 Manacor | 03/02 10:00 | 26 | Caijsa W Hennemann v Tianmi Mi | 2-6,4-6 | |
| ITF W15 Manacor | 03/01 11:00 | 25 | Caijsa W Hennemann v Marta HG Encinas | 2-6,6-3,6-1 | |
| ITF W25 Antalya | 02/01 07:00 | 25 | Ayla Aksu v Caijsa W Hennemann | 6-2,5-7,6-4 | |
| ITF W60 Vero Beach | 01/18 18:25 | 25 | [394] Emiliana Arango v Caijsa W Hennemann [287] | 6-2,6-4 | |
| ITF W25 Naples | 01/11 15:50 | 25 | [461] Madison Sieg v Caijsa W Hennemann [283] | 6-1,6-0 | |
| WTA Angers | 12/04 16:30 | 14 | [358] Hina Inoue v Caijsa W Hennemann [285] | 5-7,6-1,6-4 | |
| ITF W25 Pétange | 11/22 15:00 | 25 | Caijsa W Hennemann v Daria Lopatetska | 6-2,4-6,2-6 | |
| ITF W25 Helsingi | 11/17 13:10 | 27 | [287] Caijsa W Hennemann v Elena Malygina [373] | 2-6,2-6 |