| ITF W25 Ortisei | 11/23 10:00 | 27 | Caijsa W Hennemann v Mona Barthel | 2-6,2-6 | |
| ITF W25 Ortisei | 11/22 11:55 | 26 | Caijsa W Hennemann v Kamilla Bartone | 7-5,6-3 | |
| ITF W25 Ortisei | 11/21 16:35 | 25 | Susan Bandecchi v Caijsa W Hennemann | 6-3,3-6,2-6 | |
| Billie Jean King Cup | 11/12 14:20 | 4 | Harriet Dart v Caijsa W Hennemann | 7-5,6-2 | |
| Billie Jean King Cup | 11/12 14:10 | 4 | Jodie Burrage v Caijsa W Hennemann | Cancelled | |
| Billie Jean King Cup | 11/11 15:45 | 2 | Katie Boulter v Caijsa W Hennemann | 6-2,6-1 | |
| ITF W15 Nasbypark | 11/04 10:55 | 28 | Caijsa W Hennemann v Andre Lukosiute | 1-6,5-7 | |
| ITF W15 Nasbypark | 11/03 11:15 | 27 | Caijsa W Hennemann v Jana Otzipka | 6-1,6-1 | |
| ITF W15 Nasbypark | 11/02 10:45 | 26 | Caijsa W Hennemann v Naima Karamoko | 7-6,6-1 | |
| ITF W15 Nasbypark | 11/01 13:00 | 25 | Caijsa W Hennemann v Anna Sofia Haseth | 6-4,6-3 | |
| ITF W25 Santa Margherita | 10/15 08:25 | 29 | [206] Sara Bejlek v Caijsa W Hennemann [465] | 6-4,7-6 | |
| ITF W25 Santa Margherita | 10/14 09:00 | 28 | [465] Caijsa W Hennemann v Irina Maria Bara [192] | 3-6,7-5,6-1 | |
| ITF W25 Santa Margherita | 10/13 09:00 | 27 | [490] Anastasia Abbagnato v Caijsa W Hennemann [465] | 3-6,3-6 | |
| ITF W25 Santa Margherita | 10/12 11:00 | 26 | [465] Caijsa W Hennemann v Veronika Erjavec [197] | 6-1,2-6,6-2 | |
| ITF W25 Santa Margherita | 10/10 14:05 | 25 | [483] Sofia Rocchetti v Caijsa W Hennemann [465] | 6-4,2-6,4-6 | |
| ITF W25 Santa Margherita | 10/05 08:45 | 26 | [209] Nuria Brancaccio v Caijsa W Hennemann [470] | 6-4,6-3 | |
| ITF W25 Santa Margherita | 10/04 10:10 | 25 | [470] Caijsa W Hennemann v Angelica Moratelli [96] | 6-2,6-4 | |
| ITF W25 Santa Margherita | 10/03 08:00 | 19 | Caijsa W Hennemann v Federica Urgesi | 7-6,3-6,10-6 | |
| ITF W25 Santa Margherita | 09/28 10:45 | 26 | [462] Caijsa W Hennemann v Carlota Martinez Cirez [233] | 5-7,5-7 | |
| ITF W25 Santa Margherita | 09/27 10:25 | 25 | [418] Aurora Zantedeschi v Caijsa W Hennemann [462] | 3-6,0-6 | |
| ITF W25 Santa Margherita | 09/20 11:35 | 25 | [500] Laura Hietaranta v Caijsa W Hennemann [463] | 0-6,6-1,6-2 | |
| ITF W25 Frydek Mistek | 09/05 10:45 | 25 | Linda Klimovicova v Caijsa W Hennemann | 6-1,6-1 | |
| ITF W25 Trieste | 08/30 11:25 | 25 | Caijsa W Hennemann v Anna Turati | 6-7,6-7 | |
| ITF W25 Horb | 07/25 13:00 | 25 | [396] Martina Colmegna v Caijsa W Hennemann [411] | 3-6,7-6,6-1 | |
| ITF W25 Darmstadt | 07/19 12:30 | 25 | Nicole Rivkin v Caijsa W Hennemann | 7-6,6-4 | |
| WTA Bastad | 07/11 15:00 | 25 | Nellie Taraba Wallberg v Caijsa W Hennemann | 3-6,6-4,6-3 | |
| ITF W25 Klosters | 07/07 10:20 | 27 | [458] Alexandra Vecic v Caijsa W Hennemann [364] | 6-1,4-6,6-2 | |
| ITF W25 Klosters | 07/06 06:55 | 26 | Victoria Muntean v Caijsa W Hennemann | 1-6,0-6 | |
| ITF W25 Klosters | 07/05 09:20 | 25 | Arlinda Rushiti v Caijsa W Hennemann | 1-6,4-6 | |
| ITF W15 Alkmaar | 07/02 10:00 | 29 | Caijsa W Hennemann v Luca Udvardy | 1-6,5-7 |