Stadium: Stadium Round: 26 Ground: Clay
| ITF M15 Vero Beach | 2021/10/20 23:35 | Donald Young v Jack Anthrop | 6-2,7-5 |
| Challenger Columbus | 2021/09/19 17:35 | Evan King v Donald Young | 7-5,4-6,6-4 |
| Challenger Cary | 2021/09/13 23:25 | Donald Young v Denis Kudla | 6-7,6-4,2-6 |
| ATP Winston-Salem | 2021/08/21 19:45 | Donald Young v Tung-Lin Wu | 0-6,0-6 |
| ATP Atlanta | 2021/07/24 15:50 | Peter Gojowczyk v Donald Young | 6-4,6-1 |
| Challenger Cary | 2021/07/19 23:00 | Stefan Kozlov v Donald Young | 4-6,6-4,6-4 |
| UTR Pro Tennis Series Atlanta | 2021/07/07 16:30 | Mac Kiger v Donald Young | 7-6,2-6,0-5 |
| UTR Pro Tennis Series Atlanta | 2021/07/06 13:30 | Andrew Rogers v Donald Young | 1-6,6-4,7-6 |
| ITF M15 Vero Beach | 2021/10/20 22:00 | Matthew Segura v Cooper Williams | 1-6,6-3,6-1 |
| UTR Pro Tennis Series Florida | 2021/09/19 14:00 | Matthew Segura v Roman Postolka | 1-1 |
| UTR Pro Tennis Series Florida | 2021/09/18 17:30 | Matthew Segura v Brian Berdusco | 6-3,5-2 |
| UTR Pro Tennis Series Florida | 2021/09/17 22:30 | Matthew Segura v Meecah Bigun | 6-1,6-4 |
| UTR Pro Tennis Series Florida | 2021/09/15 16:30 | Matthew Segura v Rafael Lima Wagner | 2-6,6-3,5-1 |
| UTR Pro Tennis Series Florida | 2021/09/15 12:00 | Matthew Segura v Michal Lusovsky | 6-4,4-6,4-5 |
| UTR Pro Tennis Series Florida | 2021/09/13 12:00 | Noureldin Adam v Matthew Segura | 3-6,6-2,2-5 |
| UTR Pro Tennis Series Florida | 2021/09/11 15:00 | Rubin Statham v Matthew Segura | 6-2,6-4 |