Stadium: Court 1 Round: 19 Ground: Clay
| ITF W15 Fukui | 2023/04/25 02:00 | Mio Mushika v Jessup, Madeleine | 6-1,6-3 |
| Osaka, Singles W-ITF-JPN-02A | 2023/04/18 01:00 | Nanari Katsumi v Jessup, Madeleine | 6-4,0-6,1-10 |
| ITF - W15 Sharm El Sheikh | 2022/11/03 12:40 | BoYoung Jeong v Jessup, Madeleine | 7-5,6-0 |
| ITF - W15 Sharm El Sheikh | 2022/11/02 11:05 | Jessup, Madeleine v Nahia Berecoechea | 6-4,6-4 |
| ITF - W15 Sharm El Sheikh | 2022/10/28 08:00 | Jessup, Madeleine v Andre Lukosiute | 5-7,3-6 |
| ITF - W15 Sharm El Sheikh | 2022/10/27 08:00 | Han Shi v Jessup, Madeleine | 4-6,2-6 |
| ITF - W15 Sharm El Sheikh | 2022/10/26 12:50 | Ersoz, Vanessa v Jessup, Madeleine | 0-6,0-6 |
| ITF - W15 Sharm El Sheikh | 2022/10/22 08:00 | Andre Lukosiute v Jessup, Madeleine | 6-0,6-3 |