Estadio: Stadium Court Round: 19 Ground: Clay
| Challenger de Columbus | 2022/09/19 18:00 | Donald Young v Patrick Kypson | 6-4,0-6,4-6 |
| Challenger de Newport Beach | 2019/01/21 18:00 | Patrick Kypson v Donald Young | 3-6,2-6 |
| Challenger de Tallahassee | 2023/04/16 17:00 | Patrick Kypson v John Bernard | 6-3,7-5 |
| Challenger de San Luis Potosí | 2023/04/08 23:00 | Tomas Barrios Vera v Patrick Kypson | 6-4,6-3 |
| Challenger de San Luis Potosí | 2023/04/07 21:30 | Patrick Kypson v Terence Atmane | 6-2,6-7,6-2 |
| Challenger de San Luis Potosí | 2023/04/07 17:35 | Rodrigo Pacheco Mendez v Patrick Kypson | 3-6,3-6 |
| Challenger de San Luis Potosí | 2023/04/05 01:50 | Adolfo Daniel Vallejo v Patrick Kypson | 1-6,3-6 |
| Challenger de San Luis Potosí | 2023/04/03 20:20 | Alexis Galarneau v Patrick Kypson | 4-6,3-6 |
| Challenger de San Luis Potosí | 2023/04/02 20:30 | Patrick Kypson v Dmitry Popko | 6-1,6-2 |
| ITF M25 Mosquera | 2023/03/23 18:15 | Patrick Kypson v Gonzalo Lama | 6-4,6-7,4-6 |
| Challenger de Tallahassee | 2023/04/16 17:00 | Donald Young v Aidan Mayo | 6-4,2-6,6-4 |
| Challenger de Sarasota | 2023/04/10 17:10 | Zachary Svajda v Donald Young | 7-5,1-6,6-1 |
| Challenger de Rome GA | 2023/02/20 17:30 | Keegan Smith v Donald Young | 6-4,6-3 |
| Challenger de Rome GA | 2023/02/19 19:25 | Donald Young v Kiranpal Pannu | 5-7,6-2,6-2 |
| Challenger de Cleveland | 2023/01/29 19:20 | Donald Young v Thai-Son Kwiatkowski | 3-6,1-6 |
| Challenger de Knoxville | 2022/11/07 19:25 | Donald Young v Tristan McCormick | 6-3,4-6,5-7 |
| Challenger de Charlottesville | 2022/10/30 14:00 | Tristan McCormick v Donald Young | 4-6,3-6 |
| Challenger de Las Vegas | 2022/10/24 17:30 | Simon Carr v Donald Young | 3-6,6-3,6-3 |