Stadium: Court 4 Round: 25 Ground: Hardcourt outdoor
| Challenger Granby | 2023/07/17 16:05 | Nick Chappell v Alexander Cozbinov | 7-6,0-6,7-6 |
| Challenger Granby | 2023/07/16 21:20 | Nick Chappell v Keegan Rice | 6-1,6-3 |
| ITF M25 Dallas | 2023/07/11 21:30 | Alexander Bernard v Nick Chappell | 1-6,6-4,3-6 |
| Challenger Bloomfield Hills | 2023/07/03 20:55 | Justin Boulais v Nick Chappell | 4-6,7-5,6-4 |
| ITF M25 Santo Domingo | 2023/07/01 13:30 | Liam Draxl v Nick Chappell | 7-6,6-1 |
| ITF M25 Santo Domingo | 2023/06/30 13:30 | Darian King v Nick Chappell | 2-6,2-6 |
| ITF M25 Santo Domingo | 2023/06/29 13:30 | Joshua Lapadat v Nick Chappell | 6-3,6-7,2-6 |
| ITF M25 Santo Domingo | 2023/06/28 18:50 | Brandon Perez v Nick Chappell | 4-6,1-6 |
| Challenger Chicago | 2023/07/10 16:50 | Yunseong Chung v Thai-Son Kwiatkowski | 6-0,3-6,6-3 |
| Challenger Chicago | 2023/07/09 21:05 | Thai-Son Kwiatkowski v Aidan Mchugh | 7-5,3-6,7-6 |
| Challenger Cali | 2023/06/19 21:05 | Tristan Schoolkate v Thai-Son Kwiatkowski | 7-6,7-5 |
| Challenger Tyler | 2023/06/08 17:55 | Nicolas Moreno De Alboran v Thai-Son Kwiatkowski | 6-4,6-2 |
| Challenger Tyler | 2023/06/06 16:45 | Daniel Masur v Thai-Son Kwiatkowski | 6-7,6-7 |
| Challenger Little Rock | 2023/06/02 17:45 | Antoine Escoffier v Thai-Son Kwiatkowski | 6-1,3-6,7-5 |
| Challenger Little Rock | 2023/05/31 23:00 | Thai-Son Kwiatkowski v Daniel Masur | 7-5,6-4 |
| Challenger Little Rock | 2023/05/29 18:45 | Thai-Son Kwiatkowski v Viktor Durasovic | 6-4,7-5 |