Stadium: Court 1 Round: 19 Ground: Hardcourt indoor
| Challenger Tallahassee | 2021/04/20 14:00 | Ryan Harrison v Donald Young | 2-6,6-3,6-3 |
| ATP New York | 2018/02/13 00:30 | Ryan Harrison v Donald Young | 6-3,7-6 |
| ATP Memphis | 2017/02/19 01:30 | Ryan Harrison v Donald Young | 6-4,6-4 |
| Others | 2016/10/02 05:00 | Donald Young v Ryan Harrison | 7-5,1-6,4-6 |
| ATP Houston | 2014/04/08 18:40 | Ryan Harrison v Donald Young | 0-6,1-6 |
| Challenger Las Vegas | 2021/10/26 22:05 | Donald Young v Tatsuma Ito | 4-6,4-6 |
| Challenger Las Vegas | 2021/10/25 18:00 | Michael Redlicki v Donald Young | 6-7,6-1,6-7 |
| Challenger Las Vegas | 2021/10/24 17:00 | Donald Young v Darian King | 6-3,3-6,6-4 |
| 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 |
| ITF M15 Naples | 2021/10/10 14:00 | Antoine Cornut-Chauvinc v Ryan Harrison | 3-6,5-7 |
| ITF M15 Naples | 2021/10/09 14:00 | Damien Wenger v Ryan Harrison | 3-6,5-7 |
| ITF M15 Naples | 2021/10/08 14:30 | Peter Bertran v Ryan Harrison | 3-6,1-6 |
| ITF M15 Naples | 2021/10/07 15:35 | Juncheng Shang v Ryan Harrison | 3-6,2-6 |
| ITF M15 Naples | 2021/10/06 19:25 | Louroi Martinez v Ryan Harrison | 6-7,3-6 |
| Challenger Barletta | 2021/08/23 11:00 | Luca Potenza v Ryan Harrison | 3-6,6-3,2-6 |
| Challenger Barletta | 2021/08/22 12:50 | Ryan Harrison v Alexis Galarneau | 6-4,6-3 |
| ITF M25 Ueberlingen | 2021/08/20 11:30 | Ryan Harrison v Eduard Esteve Lobato | 1-6,4-6 |