Stadium: Court 15 Round: 19 Ground: Hardcourt outdoor
| Challenger Seoul | 2023/04/26 02:00 | Thai-Son Kwiatkowski v Denis Kudla | 1-6,0-6 |
| Challenger Tallahassee | 2023/04/21 17:45 | Tung-Lin Wu v Thai-Son Kwiatkowski | 4-6,6-4,6-3 |
| Challenger Tallahassee | 2023/04/20 22:00 | Kyle Kang v Thai-Son Kwiatkowski | 4-6,4-6 |
| Challenger Tallahassee | 2023/04/18 23:20 | Thai-Son Kwiatkowski v Dominik Koepfer | 3-6,6-3,6-4 |
| ITF M15 Sunrise | 2023/04/16 14:00 | Tristan McCormick v Thai-Son Kwiatkowski | 4-6,6-7 |
| ITF M15 Sunrise | 2023/04/15 16:40 | Jaycer Lyeons v Thai-Son Kwiatkowski | 6-7,1-6 |
| ITF M15 Sunrise | 2023/04/14 14:05 | Thai-Son Kwiatkowski v Sekou Bangoura | 6-3,6-4 |
| ITF M15 Sunrise | 2023/04/13 15:00 | Federico Agustin Gomez v Thai-Son Kwiatkowski | 4-6,2-6 |
| Challenger Puerto Vallarta | 2023/03/06 21:00 | James McCabe v Keegan Smith | 6-7,7-6,6-3 |
| Challenger Puerto Vallarta | 2023/03/05 18:30 | Keegan Smith v Daniel Cukierman | 6-3,6-3 |
| Challenger Waco | 2023/02/28 18:00 | Keegan Smith v Alex Bolt | 3-6,4-6 |
| Challenger Waco | 2023/02/27 18:55 | Keegan Smith v Elmar Ejupovic | 6-3,7-6 |
| Challenger Rome GA | 2023/02/21 18:10 | Patrick Kypson v Keegan Smith | 6-1,7-6 |
| Challenger Rome GA | 2023/02/20 17:30 | Keegan Smith v Donald Young | 6-4,6-3 |
| Challenger Rome GA | 2023/02/19 22:05 | Keegan Smith v Benjamin Sigouin | 6-3,6-4 |
| Challenger Cleveland | 2023/01/30 21:35 | Keegan Smith v Kyle Seelig | 6-2,4-6,4-6 |