Stadium: Court 3 Round: 25 Ground: Hardcourt indoor
| Challenger Cary | 2019/09/11 16:50 | Thai-Son Kwiatkowski v Brandon Nakashima | 6-7,4-6 |
| Challenger New Haven | 2019/09/04 14:00 | Thai-Son Kwiatkowski v Tommy Paul | 6-7,4-6 |
| Challenger New Haven | 2019/09/03 17:45 | Thai-Son Kwiatkowski v Colin Sinclair | 7-6,6-2 |
| US Open | 2019/08/19 15:00 | Mikael Ymer v Thai-Son Kwiatkowski | 5-7,6-3,7-6 |
| ATP Montreal | 2019/08/03 15:00 | Daniel Evans v Thai-Son Kwiatkowski | 7-6,6-1 |
| ATP Washington | 2019/07/31 01:25 | Thai-Son Kwiatkowski v Nick Kyrgios | 5-7,4-6 |
| ATP Washington | 2019/07/28 16:00 | Viktor Troicki v Thai-Son Kwiatkowski | 3-6,7-6,4-6 |
| ATP Washington | 2019/07/27 14:00 | Thai-Son Kwiatkowski v Noah Rubin | 7-5,4-6,6-1 |
| Challenger Columbus 3 | 2019/09/16 20:10 | Evan Song v Cannon Kingsley | 4-6,6-2,2-6 |
| ITF M25 Champaign | 2019/07/26 21:00 | Cannon Kingsley v Aleksandar Kovacevic | 4-6,4-6 |
| ITF M25 Champaign | 2019/07/25 17:00 | Cannon Kingsley v Michael Shabaz | 6-7,6-2,6-4 |
| ITF M25 Champaign | 2019/07/23 18:35 | Cannon Kingsley v William Bushamuka | 6-3,6-4 |
| Challenger Columbus | 2019/06/10 22:45 | Cannon Kingsley v Ji Sung Nam | 5-7,4-6 |
| Challenger Savannah | 2019/05/01 15:15 | Cannon Kingsley v Corentin Moutet | 1-6,1-6 |
| Challenger Savannah | 2019/04/30 14:00 | Cannon Kingsley v Johannes Haerteis | 6-2,6-2 |
| ITF M15 Orange Park | 2019/04/18 15:00 | Agustin Velotti v Cannon Kingsley | 5-7,6-2,6-3 |