Stadium: Stadium Round: 25 Ground: Hardcourt outdoor
| Challenger Rome GA | 2023/02/21 18:10 | Patrick Kypson v Keegan Smith | 6-1,7-6 |
| 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 |
| Challenger Savannah | 2023/04/28 17:45 | Patrick Kypson v Nicolas Kicker | 6-2,6-3 |
| Challenger Savannah | 2023/04/26 15:00 | Patrick Kypson v Evan Zhu | 4-6,6-2,6-1 |
| Challenger Savannah | 2023/04/24 18:45 | Alex Michelsen v Patrick Kypson | 6-4,3-6,6-7 |
| Challenger Tallahassee | 2023/04/19 23:25 | Patrick Kypson v Zizou Bergs | 2-6,2-6 |
| Challenger Tallahassee | 2023/04/18 17:55 | Patrick Kypson v Ulises Blanch | 6-3,7-5 |
| Challenger Tallahassee | 2023/04/17 17:25 | Patrick Kypson v Donald Young | 6-0,6-2 |
| Challenger Tallahassee | 2023/04/16 17:00 | Patrick Kypson v John Bernard | 6-3,7-5 |
| Challenger San Luis Potosi | 2023/04/08 23:00 | Tomas Barrios Vera v Patrick Kypson | 6-4,6-3 |