Results
| ITF W15 Luan | 07/16 01:00 | - | Varvara Panshina v Madeleine Jessup | 6-2,6-1 | |
| ITF W35 Taipei | 06/23 03:30 | - | Madeleine Jessup v Yu-Yun Li | 1-6,1-6 | |
| ITF W35 Taipei | 06/18 03:30 | - | Yeonwoo Ku v Madeleine Jessup | 6-0,6-0 | |
| ITF W35 Taipei | 06/16 02:00 | - | Belle Thompson v Madeleine Jessup | 5-7,1-6 | |
| UTR Pro Taiwan Women | 06/12 02:50 | 28 | Madeleine Jessup v Shiori Takeda | CANC | |
| UTR Pro Taiwan Women | 06/11 07:00 | - |
Madeleine Jessup v
Kaylah McPhee
|
Walkover | |
| UTR Pro Taiwan Women | 06/11 01:00 | - | Madeleine Jessup v Kei Yau Cheung | Retired | |
| UTR Pro Taiwan Women | 06/10 01:30 | - | Madeleine Jessup v Whitney Moon | 6-1,6-2 | |
| ITF W15 Wuning | 04/23 03:30 | - |
Yidi Yang
v
Madeleine Jessup |
6-2,6-1 | |
| UTR Pro Kaohsiung Women | 03/28 02:35 | 29 | Madeleine Jessup v Junri Namigata | 3-6,2-6 | |
| UTR Pro Kaohsiung Women | 03/27 03:50 | 28 | Mana Ayukawa v Madeleine Jessup | Walkover | |
| UTR Pro Kaohsiung Women | 03/26 03:50 | - | Yu Yun Tsai v Madeleine Jessup | 2-6,6-3,5-7 |