Stadium: Centre Court Round: 24 Ground: Hardcourt outdoor
| Challenger - Lexington | 2019/08/01 14:00 | Benjamin Sigouin v JC Aragone | 3-6,2-6 |
| ITF Canada F4 | 2018/06/30 20:00 | JC Aragone v Benjamin Sigouin | 6-1,6-7,6-4 |
| Challenger Aptos | 2019/08/05 22:30 | JC Aragone v Evan Hoyt | 4-6,2-6 |
| Challenger - Lexington | 2019/08/03 19:10 | JC Aragone v Jannik Sinner | 2-6,4-6 |
| Challenger - Lexington | 2019/08/02 16:35 | JC Aragone v Akira Santillan | 7-6,7-6 |
| Challenger - Lexington | 2019/08/01 14:00 | Benjamin Sigouin v JC Aragone | 3-6,2-6 |
| Challenger - Lexington | 2019/07/31 17:30 | Sebastian Korda v JC Aragone | 6-7,4-6 |
| Challenger Binghamton | 2019/07/24 21:30 | Maxime Cressy v JC Aragone | 7-6,4-6,6-3 |
| Challenger Winnetka | 2019/07/11 18:50 | JC Aragone v Ramkumar Ramanathan | 6-7,3-6 |
| Challenger Winnetka | 2019/07/10 20:15 | Mitchell Krueger v JC Aragone | 6-2,6-7,6-7 |
| 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 |
| Challenger - Granby | 2019/07/23 22:30 | Benjamin Sigouin v Hiroki Moriya | 3-6,7-6,3-6 |
| Challenger - Granby | 2019/07/22 22:30 | Taha Baadi v Benjamin Sigouin | 7-6,4-6,2-6 |
| Challenger Gatineau | 2019/07/16 00:45 | Borna Gojo v Benjamin Sigouin | 5-7,6-3,6-2 |
| Challenger Winnipeg | 2019/07/10 21:55 | Benjamin Sigouin v Norbert Gombos | 6-7,3-6 |
| Challenger Winnipeg | 2019/07/10 15:00 | Benjamin Sigouin v Carlos Gomez-Herrera | 6-2,3-6,6-3 |