Stadium: Court 15 Round: 19 Ground: Hardcourt outdoor
| Challenger Cary | 2023/08/06 20:00 | Nicolas Mejia v Ryan Harrison | 3-6,4-6 |
| ATP Washington | 2023/07/29 14:00 | Ryan Harrison v Zachary Svajda | 3-6,6-7 |
| Challenger Tallahassee | 2023/04/17 14:00 | Kaylan Bigun v Ryan Harrison | 2-6,6-7 |
| Challenger Sarasota | 2023/04/10 00:45 | Guido Andreozzi v Ryan Harrison | 6-3,6-3 |
| Challenger Waco | 2023/02/28 21:10 | Ryan Harrison v Aleksandar Kovacevic | 3-6,6-7 |
| Challenger Rome GA | 2023/02/22 16:35 | Ryan Harrison v Elmar Ejupovic | 6-3,6-7,2-6 |
| Challenger Rome GA | 2023/02/20 21:40 | Illya Marchenko v Ryan Harrison | 3-6,6-3,3-6 |
| Challenger Cleveland | 2023/02/02 17:45 | Stefan Kozlov v Ryan Harrison | 6-4,6-4 |
| Challenger Cary | 2023/08/06 21:30 | Michail Pervolarakis v Blake Ellis | 3-6,2-6 |
| Challenger Lexington | 2023/07/31 17:15 | Blake Ellis v Stefan Dostanic | 4-6,4-6 |
| Challenger Lexington | 2023/07/30 20:00 | Blake Ellis v Noah Schachter | 6-4,6-7,6-4 |
| Challenger Salinas | 2023/07/24 15:00 | Blake Ellis v Matija Pecotic | 3-6,6-4,1-6 |
| Challenger Salinas | 2023/07/23 17:25 | Blake Ellis v Alejandro H Franco | 6-3,6-2 |
| Challenger Granby | 2023/07/17 17:00 | Blaise Bicknell v Blake Ellis | 6-1,6-0 |
| Challenger Granby | 2023/07/17 01:00 | Blake Ellis v Ajeet Rai | 5-7,6-4,7-5 |
| ITF M25 Dallas | 2023/07/15 15:50 | Blake Ellis v Mitchell Krueger | 7-5,6-7,2-6 |