Stadium: Court 5 Round: 1
| Billie Jean King Cup | 2023/07/26 03:05 | Madeleine Jessup v Fremont Gibson | 6-2,6-1 |
| UTR Pro - Taipei - Feminin | 2023/07/20 04:30 | Madeleine Jessup v Daria Lodikova | 3-6,1-4 |
| UTR Pro - Taipei - Feminin | 2023/07/19 01:00 | Deanne Choo v Madeleine Jessup | 1-6,3-6 |
| UTR Pro - Taipei - Feminin | 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 |