Stadium: Court 1 Round: 25 Ground: Clay
| New York, USA | 2018/02/13 00:30 | Harrison, Ryan v Young, Donald | 6-3,7-6 |
| ATP Memphis | 2017/02/19 01:30 | Harrison, Ryan v Young, Donald | 6-4,6-4 |
| Others | 2016/10/02 05:00 | Young, Donald v Harrison, Ryan | 7-5,1-6,4-6 |
| ATP - Houston | 2014/04/08 18:40 | Harrison, Ryan v Young, Donald | 0-6,1-6 |
| ATP - Delray Beach | 2021/01/07 19:30 | Gianluca Mager v Harrison, Ryan | 3-6,6-1,6-4 |
| ATP - Acapulco | 2020/02/23 01:00 | Daniel Altmaier v Harrison, Ryan | 6-2,6-3 |
| ATP - Delray Beach | 2020/02/19 17:30 | Soonwoo Kwon v Harrison, Ryan | 6-4,3-6,7-6 |
| ATP - Delray Beach | 2020/02/17 17:45 | Harrison, Ryan v Damir Dzumhur | 6-3,6-2 |
| Challenger - Cleveland | 2020/02/13 19:55 | Geoffrey Blancaneaux v Harrison, Ryan | 6-3,3-6,6-2 |
| Challenger - Cleveland | 2020/02/13 00:05 | Harrison, Ryan v Sebastian Ofner | 6-3,6-7,6-3 |
| Challenger - Cleveland | 2020/02/10 23:00 | Harrison, Ryan v Collin Altamirano | 6-4,7-6 |
| Challenger Dallas | 2020/02/04 03:00 | Harrison, Ryan v Brandon Nakashima | 3-6,4-6 |
| Challenger - Tallahassee | 2021/04/19 15:00 | Young, Donald v Filip Cristian Jianu | 4-6,2-6 |
| Challenger - Tallahassee | 2021/04/18 20:00 | Young, Donald v King, Evan | 6-1,6-2 |
| Challenger - Cleveland | 2021/03/17 23:35 | Alexis Galarneau v Young, Donald | 7-5,7-5 |
| Challenger - Cleveland | 2021/03/15 20:25 | Young, Donald v Soeda, Go | 6-3,6-7,7-5 |
| ATP - Delray Beach | 2021/01/09 01:30 | Frances Tiafoe v Young, Donald | 6-3,6-4 |
| ATP - Delray Beach | 2021/01/06 16:00 | Young, Donald v Stefan Kozlov | 4-6,6-4,6-4 |
| ATP - Delray Beach | 2021/01/05 15:40 | Pedro Sakamoto v Young, Donald | 6-3,4-6,2-6 |
| GTS Atlanta Exhibition | 2020/09/18 15:00 | Young, Donald v Pasha, Nathan | 6-3,7-5 |