| ITF W25 Helsingi | 11/16 14:00 | 26 | [287] Caijsa W Hennemann v Julia Middendorf [400] | 6-3,6-3 | |
| ITF W25 Helsingi | 11/15 14:55 | 25 | Caijsa W Hennemann v Bibiane Schoofs | 6-4,7-5 | |
| ITF W25 Loughborough | 10/25 13:25 | 25 | Caijsa W Hennemann v Yeonwoo Ku | Cancelled | |
| ITF W25 Loule | 10/22 16:05 | 27 | [152] Victoria Jimenez Kasintseva v Caijsa W Hennemann [300] | 1-6,6-3,6-4 | |
| ITF W25 Loule | 10/21 14:00 | 26 | Caijsa W Hennemann v Yvonne Cavalle-Reimers | 6-2,6-3 | |
| ITF W25 Loule | 10/18 13:15 | 25 | [497] Valentina Ryser v Caijsa W Hennemann [300] | 6-2,6-7,2-6 | |
| ITF W25 Santa Margherita | 10/09 07:30 | 29 | [156] Ylena In-Albon v Caijsa W Hennemann [347] | 1-6,5-7 | |
| ITF W25 Santa Margherita | 10/08 12:00 | 28 | [347] Caijsa W Hennemann v Katharina Hobgarski [218] | 6-2,2-6,6-4 | |
| ITF W25 Santa Margherita | 10/07 11:00 | 27 | [347] Caijsa W Hennemann v Nastasja M Schunk [208] | 6-2,6-3 | |
| ITF W25 Santa Margherita | 10/06 12:35 | 26 | [269] Darja Semenistaja v Caijsa W Hennemann [347] | 3-6,3-6 | |
| ITF W25 Santa Margherita | 10/05 13:35 | 25 | [306] Noma Noha Akugue v Caijsa W Hennemann [347] | 3-6,2-6 | |
| ITF W25 Santa Margherita | 09/29 16:05 | 26 | [349] Caijsa W Hennemann v Darja Semenistaja [286] | 5-7,1-6 | |
| ITF W25 Santa Margherita | 09/27 20:05 | 25 | [357] Hurricane Tyra Black v Caijsa W Hennemann [349] | 2-6,1-6 | |
| ITF W25 Santa Margherita | 09/20 15:25 | 25 | [275] Camilla Rosatello v Caijsa W Hennemann [347] | 6-2,6-4 | |
| ITF W25 Saint-Palais-sur-Mer | 09/06 14:45 | 25 | [335] Caijsa W Hennemann v Audrey Albie [368] | 1-6,2-6 | |
| ITF W60 Praha | 08/29 13:15 | 24 | Caijsa W Hennemann v Linda Klimovicova | Retired | |
| ITF W25 Oldenzaal | 08/25 08:00 | 26 | Kajsa Rinaldo Persson v Caijsa W Hennemann | 6-3,6-0 | |
| ITF W25 Oldenzaal | 08/23 16:50 | 25 | Demi Tran v Caijsa W Hennemann | Retired | |
| ITF W25 Danderyd | 08/10 08:10 | 25 | Lisa Zaar v Caijsa W Hennemann | 6-3,7-5 | |
| ITF W25 Eupen | 08/06 13:00 | 28 | [352] Caijsa W Hennemann v Marie Benoit [362] | 4-6,5-7 | |
| ITF W25 Eupen | 08/05 12:00 | 27 | [356] Anna Turati v Caijsa W Hennemann [352] | 2-6,6-3,4-6 | |
| ITF W25 Eupen | 08/04 13:35 | 26 | Berta Bonardi v Caijsa W Hennemann | 1-6,2-6 | |
| ITF W25 Eupen | 08/03 15:50 | 25 | Amelie Van Impe v Caijsa W Hennemann | 5-7,1-6 | |
| WTA Bastad | 07/06 09:00 | 26 | [388] Caijsa W Hennemann v Panna Udvardy [100] | 4-6,2-6 | |
| WTA Bastad | 07/05 08:30 | 25 | [194] Renata Zarazua v Caijsa W Hennemann [388] | 4-6,6-2,1-6 | |
| ITF W25 Den Haag | 07/02 10:00 | 28 | [388] Caijsa W Hennemann v Magali Kempen [358] | 2-6,4-6 | |
| ITF W25 Den Haag | 07/01 11:00 | 27 | [388] Caijsa W Hennemann v Eva Vedder [293] | 6-3,6-4 | |
| ITF W25 Den Haag | 06/30 11:00 | 26 | [169] Suzan Lamens v Caijsa W Hennemann [388] | 5-7,6-2,3-6 | |
| ITF W25 Den Haag | 06/28 11:10 | 25 | [479] Merel Hoedt v Caijsa W Hennemann [388] | 2-6,7-6,4-6 | |
| ITF W25 Ystad | 06/23 09:50 | 26 | Caijsa W Hennemann v Daria Lopatetska | 4-6,2-6 |