Stadium: Center Court Round: 24 Ground: Hardcourt outdoor
| Challenger Columbus 3 | 2019/09/19 16:50 | Donald Young v Roberto Quiroz | 7-5,4-6,4-6 |
| Challenger Columbus 3 | 2019/09/18 18:10 | Donald Young v Gonzalo Escobar | 6-2,6-7,6-1 |
| Challenger Cary | 2019/09/12 16:30 | Donald Young v Enzo Couacaud | 1-6,6-3,3-6 |
| Challenger Cary | 2019/09/10 16:15 | Donald Young v Renzo Olivo | 6-4,6-3 |
| Challenger New Haven | 2019/09/04 19:20 | Denis Istomin v Donald Young | 6-4,6-3 |
| Challenger New Haven | 2019/09/02 15:25 | Donald Young v Filip Peliwo | 6-3,6-4 |
| US Open | 2019/08/20 16:15 | Donald Young v Jason Jung | 3-6,7-6,5-7 |
| Challenger Aptos | 2019/08/05 20:20 | Donald Young v Lukas Lacko | 4-6,2-6 |
| Challenger Columbus 3 | 2019/09/18 15:40 | Roy Smith v Ryan Shane | 4-6,6-4,6-4 |
| Challenger Columbus 3 | 2019/09/17 14:00 | Jacob Dunbar v Ryan Shane | 5-7,4-6 |
| Challenger New Haven | 2019/09/04 14:00 | Mitchell Krueger v Ryan Shane | 3-6,4-6 |
| Challenger New Haven | 2019/09/02 14:00 | Aleksandar Kovacevic v Ryan Shane | 4-6,4-6 |
| ITF M25 - Edwardsville | 2019/08/07 16:10 | Ryan Shane v Jacob Dunbar | 2-6,2-6 |
| Challenger Lexington | 2019/07/30 14:30 | Ryan Shane v Vasil Kirkov | 3-6,6-1,3-6 |
| Challenger Binghamton | 2019/07/23 16:30 | Ryan Shane v Alejandro Tabilo | 3-6,4-6 |
| Challenger Winnetka | 2019/07/09 01:50 | Sekou Bangoura v Ryan Shane | 7-5,6-3 |