Stadium: Court 3 Round: 26 Ground: Hardcourt indoor
| 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 |
| 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 |
| Challenger Columbus 3 | 2019/09/18 14:00 | Benjamin Sigouin v Renzo Olivo | 6-1,6-2 |
| Challenger Columbus 3 | 2019/09/17 15:50 | Gage Brymer v Benjamin Sigouin | 4-6,1-6 |
| Challenger Cary | 2019/09/09 21:30 | Daniel Nguyen v Benjamin Sigouin | 6-1,6-3 |
| Challenger Vancouver | 2019/08/14 19:40 | Marc Polmans v Benjamin Sigouin | 6-3,6-4 |
| Challenger Vancouver | 2019/08/13 04:15 | JC Aragone v Benjamin Sigouin | 3-6,1-6 |
| Challenger Lexington | 2019/08/01 14:00 | Benjamin Sigouin v JC Aragone | 3-6,2-6 |
| Challenger Lexington | 2019/07/31 21:05 | Peter Polansky v Benjamin Sigouin | 4-6,4-6 |
| Challenger Lexington | 2019/07/29 16:45 | Benjamin Sigouin v Ronald Hohmann | 6-1,6-4 |