Stadium: Court 5 Round: 1
| Billie Jean King Cup 2022, Finals | 2023/07/26 03:05 | Jessup, Madeleine v Fremont Gibson | 6-2,6-1 |
| UTR Pro Taipei Women | 2023/07/20 04:30 | Jessup, Madeleine v 로디코바, 다리아 | 3-6,1-4 |
| UTR Pro Taipei Women | 2023/07/19 01:00 | 추, 딘 v Jessup, Madeleine | 1-6,3-6 |
| UTR Pro Taipei Women | 2023/07/18 01:00 | Hsuan Huang v Jessup, Madeleine | 3-6,2-6 |
| ITF W25 Tainan | 2023/06/13 03:50 | 페테카우, 이리나 v Jessup, Madeleine | 6-1,6-1 |
| ITF W25 Tainan | 2023/06/12 02:00 | Jessup, Madeleine v Yu Hua Cheng | 6-1,6-3 |
| ITF W15 Fukui | 2023/04/25 02:00 | Mushika, Mio v Jessup, Madeleine | 6-1,6-3 |
| Osaka, Singles W-ITF-JPN-02A | 2023/04/18 01:00 | Katsumi, Nanari v Jessup, Madeleine | 6-4,0-6,1-10 |