Stadium: 1 Round: 2
| UTR - Pro Taipei - Dames | 2023/07/20 04:30 | Madeleine Jessup v Daria Lodikova | 3-6,1-4 |
| UTR - Pro Taipei - Dames | 2023/07/19 01:00 | Deanne Choo v Madeleine Jessup | 1-6,3-6 |
| UTR - Pro Taipei - Dames | 2023/07/18 01:00 | Hsuan Huang v Madeleine Jessup | 3-6,2-6 |
| ITF - W25 Tainan | 2023/06/13 03:50 | Irina Fetecau v Madeleine Jessup | 6-1,6-1 |
| ITF - W25 Tainan | 2023/06/12 02:00 | Madeleine Jessup v Yu Hua Cheng | 6-1,6-3 |
| ITF - W15 Fukui | 2023/04/25 02:00 | Mio Mushika v Madeleine Jessup | 6-1,6-3 |
| ITF W25 - Osaka | 2023/04/18 01:00 | Nanari Katsumi v Madeleine Jessup | 6-4,0-6,1-10 |
| ITF - W15 Sharm-el-Sheikh | 2022/11/03 12:40 | BoYoung Jeong v Madeleine Jessup | 7-5,6-0 |
| Billie Jean King Cup | 2023/07/25 03:15 | Ho Ching Wu v Fremont Gibson | 6-2,6-1 |
| Billie Jean King Cup | 2023/07/24 03:15 | Sarah Ibrahim Khan v Fremont Gibson | 3-6,4-6 |
| Billie Jean King Cup | 2022/08/24 05:10 | Rukshika Wijesooriya v Fremont Gibson | 6-0,6-2 |
| Billie Jean King Cup | 2022/08/23 05:15 | Akgul Amanmuradova v Fremont Gibson | 6-0,6-0 |