Stadium: Center Court Round: 14 Ground: Hardcourt outdoor
| Challenger Cleveland | 2023/01/29 19:20 | Donald Young v Thai-Son Kwiatkowski | 3-6,1-6 |
| Challenger Indian Wells | 2019/02/25 19:30 | Thai-Son Kwiatkowski v Donald Young | 6-4,1-6,6-7 |
| Challenger Cary | 2023/09/13 17:00 | Donald Young v Christian Langmo | 5-7,4-6 |
| Challenger Cary | 2023/09/11 17:00 | Donald Young v Kiranpal Pannu | 6-4,6-1 |
| Challenger Cary | 2023/09/10 15:00 | Federico Agustin Gomez v Donald Young | 3-6,6-3,2-6 |
| UTR Pro Knoxville | 2023/09/01 14:00 | Donald Young v Angel Diaz Jalil | 7-5,4-6,3-6 |
| UTR Pro Knoxville | 2023/08/31 16:30 | Carter Pate v Donald Young | 0-6,4-6 |
| UTR Pro Knoxville | 2023/08/30 17:32 | Tomas Luis v Donald Young | 2-6,4-6 |
| UTR Pro Knoxville | 2023/08/29 15:00 | Sabi Roi v Donald Young | 4-6,2-6 |
| UTR Pro Knoxville | 2023/08/27 17:00 | Filip Apltauer v Donald Young | 6-7,4-6 |
| Challenger Cary | 2023/09/13 17:30 | William Jansen v Thai-Son Kwiatkowski | 4-6,3-6 |
| Challenger Cary | 2023/09/11 19:10 | Thai-Son Kwiatkowski v Keegan Smith | 7-6,6-4 |
| Challenger Cary | 2023/09/10 15:00 | Thai-Son Kwiatkowski v Jibril Nettles | 6-4,6-2 |
| ATP Winston-Salem | 2023/08/21 23:25 | Luca Van Assche v Thai-Son Kwiatkowski | 3-6,6-3,6-2 |
| ATP Winston-Salem | 2023/08/20 17:00 | Thai-Son Kwiatkowski v Andrey Kuznetsov | 6-1,6-0 |
| ATP Winston-Salem | 2023/08/19 18:15 | Nick Hardt v Thai-Son Kwiatkowski | 6-7,3-6 |
| Challenger Winnipeg | 2023/08/16 18:50 | Jack Draper v Thai-Son Kwiatkowski | 6-4,7-6 |
| Challenger Winnipeg | 2023/08/15 17:30 | Thai-Son Kwiatkowski v Chris Rodesch | 6-0,6-2 |