Stadium: Court 1N Round: 26 Ground: Hardcourt outdoor
| ITF - M15 Champaign | 2023/09/12 15:00 | Liam Draxl v Atakan Karahan | 6-4,6-0 |
| ATP - Toronto | 2023/08/05 15:00 | Liam Draxl v Diego Schwartzman | 6-7,4-6 |
| ITF - M25 Laval | 2023/07/15 14:00 | Liam Draxl v Blaise Bicknell | 2-6,3-6 |
| ITF - M25 Laval | 2023/07/14 16:45 | Liam Draxl v Philip Sekulic | 7-6,6-4 |
| ITF - M25 Laval | 2023/07/13 19:10 | Liam Draxl v Sasha Rozin | 6-4,6-3 |
| ITF - M25 Laval | 2023/07/11 14:00 | Liam Draxl v Herbert Jody Maginley | 6-4,6-4 |
| ITF - M25 Santo Domingo | 2023/07/02 13:30 | Martin Damm v Liam Draxl | 7-6,6-4 |
| ITF - M25 Santo Domingo | 2023/07/01 13:30 | Liam Draxl v Nick Chappell | 7-6,6-1 |
| ITF - M15 Champaign | 2023/09/13 15:00 | Perry Gregg v Joshua Lapadat | 6-4,4-6,7-6 |
| ITF - M25 Champaign | 2023/09/12 16:40 | Pierce Rollins v Perry Gregg | 3-6,6-7 |
| ITF - M25 Champaign | 2023/09/11 15:00 | Benito Sanchez Martinez v Perry Gregg | 2-6,3-6 |
| ITF - M25 Champaign | 2023/07/19 17:40 | Perry Gregg v Ozan Baris | 5-7,4-6 |
| ITF - M25 Champaign | 2023/07/18 14:55 | Perry Gregg v Oliver Okonkwo | 3-6,6-2,10-7 |
| ITF - M15 South Bend | 2023/06/22 16:55 | Perry Gregg v James Tracy | 3-6,6-4,5-7 |
| ITF - M15 South Bend | 2023/06/21 18:40 | Perry Gregg v Fabien Salle | 6-4,6-4 |
| ITF - M15 San Diego | 2023/06/13 17:30 | Warren Wood v Perry Gregg | 6-3,7-5 |