Stadium: Center Round: 26 Ground: Hardcourt outdoor
| 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 |
| Washington, USA | 2019/07/30 01:50 | Hubert Hurkacz v Young, Donald | 6-1,6-4 |
| Washington, USA | 2019/07/28 14:00 | Gojowczyk, Peter v Young, Donald | 6-2,3-6,4-6 |
| Washington, USA | 2019/07/27 16:10 | Reyes, Nicholas Alexander v Young, Donald | 2-6,0-6 |
| Challenger Cary | 2019/09/10 20:50 | King, Kevin v Enzo Couacaud | 1-6,2-6 |
| New Haven, USA | 2019/09/04 20:15 | Enzo Couacaud v Noah Rubin | 6-0,2-6,1-6 |
| US Open, New York, USA | 2019/08/22 15:00 | Lorenzi, Paolo v Enzo Couacaud | 7-6,6-3 |
| US Open, New York, USA | 2019/08/20 16:30 | Alexey Vatutin v Enzo Couacaud | 6-7,3-6 |
| Vancouver, Canada | 2019/08/16 21:00 | Enzo Couacaud v Soeda, Go | 6-7,6-3,4-6 |
| Vancouver, Canada | 2019/08/15 20:20 | Schnur, Brayden v Enzo Couacaud | 6-7,4-6 |
| Vancouver, Canada | 2019/08/14 17:00 | Enzo Couacaud v Egor Gerasimov | 6-3,6-7,7-5 |
| Vancouver, Canada | 2019/08/13 00:05 | Enzo Couacaud v Ward, James | 1-6,6-4,6-3 |