Stadium: Centre Court Round: 24 Ground: Hardcourt outdoor
| Challenger Lexington | 2019/08/01 14:00 | Sigouin, Benjamin v Aragone, JC | 3-6,2-6 |
| ITF Canada F4 | 2018/06/30 20:00 | Aragone, JC v Sigouin, Benjamin | 6-1,6-7,6-4 |
| Challenger Aptos | 2019/08/05 22:30 | Aragone, JC v Hoyt, Evan | 4-6,2-6 |
| Challenger Lexington | 2019/08/03 19:10 | Aragone, JC v Jannik Sinner | 2-6,4-6 |
| Challenger Lexington | 2019/08/02 16:35 | Aragone, JC v Akira Santillan | 7-6,7-6 |
| Challenger Lexington | 2019/08/01 14:00 | Sigouin, Benjamin v Aragone, JC | 3-6,2-6 |
| Challenger Lexington | 2019/07/31 17:30 | Sebastian Korda v Aragone, JC | 6-7,4-6 |
| Binghamton, USA | 2019/07/24 21:30 | Maxime Cressy v Aragone, JC | 7-6,4-6,6-3 |
| Winnetka, USA | 2019/07/11 18:50 | Aragone, JC v Ramkumar Ramanathan | 6-7,3-6 |
| Winnetka, USA | 2019/07/10 20:15 | Mitchell Krueger v Aragone, JC | 6-2,6-7,6-7 |
| Challenger Lexington | 2019/08/01 14:00 | Sigouin, Benjamin v Aragone, JC | 3-6,2-6 |
| Challenger Lexington | 2019/07/31 21:05 | Polansky, Peter v Sigouin, Benjamin | 4-6,4-6 |
| Challenger Lexington | 2019/07/29 16:45 | Sigouin, Benjamin v Ronald Hohmann | 6-1,6-4 |
| Challenger Granby | 2019/07/23 22:30 | Sigouin, Benjamin v Hiroki Moriya | 3-6,7-6,3-6 |
| Challenger Granby | 2019/07/22 22:30 | Baadi, Taha v Sigouin, Benjamin | 7-6,4-6,2-6 |
| Gatineau, Canada | 2019/07/16 00:45 | Gojo, Borna v Sigouin, Benjamin | 5-7,6-3,6-2 |
| Challenger Winnipeg | 2019/07/10 21:55 | Sigouin, Benjamin v Norbert Gombos | 6-7,3-6 |
| Challenger Winnipeg | 2019/07/10 15:00 | Sigouin, Benjamin v Gomez-Herrera, Carlos | 6-2,3-6,6-3 |