Stadium: Court 1 Round: 54 Ground: Hardcourt indoor
| ITF W15 - Jackson | 2023/10/18 16:50 | Madeleine Jessup v Ania Hertel | 3-6,2-6 |
| Billie Jean King Cup | 2023/07/29 03:55 | Erin Routliffe v Madeleine Jessup | 3-6,5-7 |
| Billie Jean King Cup | 2023/07/28 05:10 | Madeleine Jessup v Ho Ching Wu | 6-4,5-7,3-6 |
| Billie Jean King Cup | 2023/07/27 02:00 | Madeleine Jessup v Amna Ali Qayum | 6-0,6-0 |
| Billie Jean King Cup | 2023/07/26 03:05 | Madeleine Jessup v Fremont Gibson | 6-2,6-1 |
| UTR Pro - Taipei - Damer | 2023/07/20 04:30 | Madeleine Jessup v Daria Lodikova | 3-6,1-4 |
| UTR Pro - Taipei - Damer | 2023/07/19 01:00 | Deanne Choo v Madeleine Jessup | 1-6,3-6 |
| UTR Pro - Taipei - Damer | 2023/07/18 01:00 | Hsuan Huang v Madeleine Jessup | 3-6,2-6 |
| ITF W15 - Norman | 2023/10/30 15:00 | Sumvruta Iyengar v Mckenna Schaefbauer | 0-6,1-6 |
| ITF W60 - Lexington | 2023/07/31 19:00 | Mckenna Schaefbauer v Alexis Blokhina | 4-6,3-6 |
| ITF W60 - Evansville | 2023/07/17 16:00 | Mckenna Schaefbauer v Danielle Willson | 5-7,0-6 |
| ITF W25 - Wichita | 2023/06/20 16:30 | Ivana Corley v Mckenna Schaefbauer | 6-2,6-4 |
| ITF W25 - Wichita | 2023/06/19 15:00 | Saniya Singh v Mckenna Schaefbauer | 2-6,1-6 |
| ITF W60 - Sumter | 2023/06/12 20:15 | Akasha Urhobo v Mckenna Schaefbauer | 6-2,6-2 |
| ITF W15 - Huntsville | 2023/05/24 17:25 | Mckenna Schaefbauer v Kolie Allen | 6-3,3-6,4-6 |
| ITF W15 - Huntsville | 2023/05/23 17:00 | Mckenna Schaefbauer v Taylor Nix | 6-2,6-0 |