Stadium: Court 4 Round: 25 Ground: Hardcourt outdoor
| Challenger Columbus 3 | 2019/09/20 17:05 | Thai-Son Kwiatkowski v Peter Polansky | 4-6,6-0,6-7 |
| Challenger Columbus 3 | 2019/09/19 15:00 | Thai-Son Kwiatkowski v Benjamin Sigouin | 6-2,6-4 |
| Challenger Columbus 3 | 2019/09/17 17:45 | Thai-Son Kwiatkowski v Cannon Kingsley | 3-6,6-4,6-3 |
| 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 |
| Challenger Tiburon | 2019/09/23 19:00 | Carlos Gomez-Herrera v Sebastian Fanselow | 6-4,4-6,6-2 |
| Challenger Columbus 3 | 2019/09/16 20:05 | Carlos Gomez-Herrera v James Trotter | 4-6,2-6 |
| Challenger Sevilla | 2019/09/10 11:00 | Kimmer Coppejans v Carlos Gomez-Herrera | 1-6,6-2,7-6 |
| Challenger Sevilla | 2019/09/09 16:00 | Carlos Gomez-Herrera v Francesco Forti | 6-4,6-3 |
| Challenger L'Aquila | 2019/08/19 14:45 | Scott Griekspoor v Carlos Gomez-Herrera | 3-6,7-6,7-6 |
| Challenger Portoroz | 2019/08/15 16:00 | Carlos Gomez-Herrera v Roman Safiullin | 2-6,4-6 |
| Challenger Portoroz | 2019/08/14 08:15 | Evgeny Karlovskiy v Carlos Gomez-Herrera | 1-6,2-6 |
| Challenger Portoroz | 2019/08/13 08:00 | Igor Sijsling v Carlos Gomez-Herrera | 2-6,3-6 |