Estadio: Court 1 Round: 28 Ground: Hardcourt indoor
| Challenger de Columbus | 2022/09/20 16:00 | Strong Kirchheimer v Gabriel Diallo | 4-6,3-6 |
| ITF M25 East Lansing | 2022/06/08 13:00 | Gabriel Diallo v Strong Kirchheimer | 6-4,6-3 |
| ITF M25 Montreal | 2023/03/17 14:00 | Gabriel Diallo v Tibo Colson | 6-2,7-5 |
| ITF M25 Montreal | 2023/03/16 15:25 | Gabriel Diallo v Aurel Ciocanu | 6-3,6-3 |
| ITF M25 Montreal | 2023/03/14 18:10 | Gabriel Diallo v Toby Alex Kodat | 6-1,6-7,7-6 |
| Challenger de Puerto Vallarta | 2023/03/08 01:30 | Yuta Shimizu v Gabriel Diallo | 4-6,6-3,7-6 |
| ATP Dallas | 2023/02/08 18:00 | Emilio Gomez v Gabriel Diallo | 6-4,6-7,7-6 |
| ATP Dallas | 2023/02/06 19:35 | Brandon Holt v Gabriel Diallo | 7-6,7-6 |
| ATP Dallas | 2023/02/05 23:05 | Antonio M-Hidalgo v Gabriel Diallo | 4-6,3-6 |
| Challenger de Cleveland | 2023/02/03 19:35 | Emilio Gomez v Gabriel Diallo | 7-6,4-6,7-5 |
| ITF M25 Montreal | 2023/03/17 13:55 | Strong Kirchheimer v Alfredo Perez | 7-6,6-3 |
| ITF M25 Montreal | 2023/03/16 17:10 | Strong Kirchheimer v James Davis | 6-1,6-3 |
| ITF M25 Montreal | 2023/03/15 14:00 | Strong Kirchheimer v Daniel Rodrigues | 6-1,6-0 |
| ITF M25 Montreal | 2023/03/12 16:00 | Jules Marie v Strong Kirchheimer | 7-5,6-0 |
| ITF M25 Montreal | 2023/03/11 16:00 | Ben Jones v Strong Kirchheimer | 0-6,4-6 |
| ITF M25 Montreal | 2023/03/10 17:10 | Benjamin Sigouin v Strong Kirchheimer | 2-6,3-6 |
| ITF M25 Montreal | 2023/03/09 15:00 | Toby Alex Kodat v Strong Kirchheimer | 6-7,3-6 |
| ITF M25 Montreal | 2023/03/08 17:40 | A.J Catanzariti v Strong Kirchheimer | 3-6,4-6 |