Stadium: Court 6 Round: 14 Ground: Hardcourt outdoor
| 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 - Santo Domingo M25 | 2023/06/27 15:30 | Justin Boulais v Evan Bynoe | 4-6,1-6 |
| ITF - Santo Domingo M15 | 2023/06/23 13:25 | Justin Boulais v Tauheed Browning | 6-4,3-6,4-6 |
| ITF - Santo Domingo M15 | 2023/06/22 17:10 | Justin Boulais v Leo Vithoontien | 6-3,6-2 |
| Challenger Granby | 2023/07/18 16:25 | Tristan Schoolkate v Joshua Sheehy | 6-2,6-3 |
| Challenger Granby | 2023/07/17 14:00 | Joshua Sheehy v Colin Markes | 6-2,6-7,7-5 |
| Challenger Granby | 2023/07/16 17:40 | Calum Puttergill v Joshua Sheehy | 4-6,6-7 |
| ITF - Dallas M25 | 2023/07/11 19:25 | Karl Poling v Joshua Sheehy | 6-4,3-6,6-3 |
| ITF - Los Angeles M15 | 2023/06/21 00:30 | Joshua Sheehy v Nicholas Godsick | 2-6,5-7 |
| ITF - San Diego M15 | 2023/06/13 21:00 | A.J Catanzariti v Joshua Sheehy | 3-6,7-5,6-4 |
| ITF - Tabasco M15 | 2023/05/26 17:00 | Ezekiel Clark v Joshua Sheehy | 6-3,6-7,7-6 |
| ITF - Tabasco M15 | 2023/05/25 17:00 | Joshua Sheehy v Andres Andrade | 4-6,6-4,6-4 |