Estadio: Center Round: 26 Ground: Hardcourt outdoor
| Challenger de Cary | 2019/09/10 16:15 | Donald Young v Renzo Olivo | 6-4,6-3 |
| Challenger de New Haven | 2019/09/04 19:20 | Denis Istomin v Donald Young | 6-4,6-3 |
| Challenger de 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 de Aptos | 2019/08/05 20:20 | Donald Young v Lukas Lacko | 4-6,2-6 |
| ATP Washington | 2019/07/30 01:50 | Hubert Hurkacz v Donald Young | 6-1,6-4 |
| ATP Washington | 2019/07/28 14:00 | Peter Gojowczyk v Donald Young | 6-2,3-6,4-6 |
| ATP Washington | 2019/07/27 16:10 | Nicholas Reyes v Donald Young | 2-6,0-6 |
| Challenger de Cary | 2019/09/10 20:50 | Kevin King v Enzo Couacaud | 1-6,2-6 |
| Challenger de New Haven | 2019/09/04 20:15 | Enzo Couacaud v Noah Rubin | 6-0,2-6,1-6 |
| US Open | 2019/08/22 15:00 | Paolo Lorenzi v Enzo Couacaud | 7-6,6-3 |
| US Open | 2019/08/20 16:30 | Alexey Vatutin v Enzo Couacaud | 6-7,3-6 |
| Challenger de Vancouver | 2019/08/16 21:00 | Enzo Couacaud v Go Soeda | 6-7,6-3,4-6 |
| Challenger de Vancouver | 2019/08/15 20:20 | Brayden Schnur v Enzo Couacaud | 6-7,4-6 |
| Challenger de Vancouver | 2019/08/14 17:00 | Enzo Couacaud v Egor Gerasimov | 6-3,6-7,7-5 |
| Challenger de Vancouver | 2019/08/13 00:05 | Enzo Couacaud v James Ward | 1-6,6-4,6-3 |