Stadium: Court 6 Round: 19 Ground: Hardcourt outdoor
| Challenger Lexington | 2023/07/30 14:00 | Justin Boulais v Joshua Sheehy | 6-2,7-5 |
| Challenger Granby | 2023/07/21 17:00 | Justin Boulais v Philip Sekulic | 3-6,2-6 |
| Challenger Granby | 2023/07/20 19:00 | Mark Lajal v Justin Boulais | 4-6,6-1,6-7 |
| Challenger Granby | 2023/07/19 00:15 | Blaise Bicknell v Justin Boulais | 0-6,6-4,4-6 |
| Challenger Bloomfield Hills | 2023/07/04 16:50 | Omar Jasika v Justin Boulais | 6-3,7-5 |
| Challenger Bloomfield Hills | 2023/07/03 20:55 | Justin Boulais v Nick Chappell | 4-6,7-5,6-4 |
| ITF M25 Santo Domingo | 2023/06/27 15:30 | Justin Boulais v Evan Bynoe | 4-6,1-6 |
| ITF M15 Santo Domingo | 2023/06/23 13:25 | Justin Boulais v Tauheed Browning | 6-4,3-6,4-6 |
| Challenger Lexington | 2023/07/30 14:00 | Taha Baadi v Jaimee Floyd Angele | 3-6,4-6 |
| ITF M25 Edwardsville | 2023/07/27 13:30 | Shunsuke Mitsui v Jaimee Floyd Angele | 3-6,6-4,6-2 |
| ITF M25 Edwardsville | 2023/07/25 17:30 | Gage Brymer v Jaimee Floyd Angele | 4-6,1-6 |
| ATP Newport | 2023/07/17 15:00 | Beibit Zhukayev v Jaimee Floyd Angele | 6-7,6-4,6-4 |
| Challenger Chicago | 2023/07/09 19:30 | Jaimee Floyd Angele v Illya Marchenko | 6-7,4-6 |
| ITF M15 Lakewood | 2023/07/08 19:30 | Andre Ilagan v Jaimee Floyd Angele | 6-2,6-2 |
| ITF M15 Lakewood | 2023/07/07 17:00 | Jaimee Floyd Angele v Karl Kazuma Lee | 7-5,6-3 |
| ITF M15 Lakewood | 2023/07/06 17:00 | Jaimee Floyd Angele v Jacob Bullard | 6-2,6-3 |