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