Stadium: Court 5 Round: 19 Ground: Clay
| Challenger Tallahassee | 2023/04/17 14:00 | Strong Kirchheimer v Mac Kiger | 6-3,4-6,6-2 |
| Challenger Sarasota | 2023/04/10 00:35 | Luca Potenza v Strong Kirchheimer | 7-6,6-3 |
| Challenger Mexico City | 2023/03/26 17:50 | Elmar Ejupovic v Strong Kirchheimer | 6-2,6-3 |
| ITF M25 Montreal | 2023/03/18 15:00 | Gabriel Diallo v Strong Kirchheimer | 6-2,7-6 |
| 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 |
| Challenger Tallahassee | 2023/04/17 14:00 | Kaylan Bigun v Ryan Harrison | 2-6,6-7 |
| Challenger Sarasota | 2023/04/10 00:45 | Guido Andreozzi v Ryan Harrison | 6-3,6-3 |
| Challenger Waco | 2023/02/28 21:10 | Ryan Harrison v Aleksandar Kovacevic | 3-6,6-7 |
| Challenger Rome GA | 2023/02/22 16:35 | Ryan Harrison v Elmar Ejupovic | 6-3,6-7,2-6 |
| Challenger Rome GA | 2023/02/20 21:40 | Illya Marchenko v Ryan Harrison | 3-6,6-3,3-6 |
| Challenger Cleveland | 2023/02/02 17:45 | Stefan Kozlov v Ryan Harrison | 6-4,6-4 |
| Challenger Cleveland | 2023/02/01 00:15 | Ryan Harrison v Jaimee Floyd Angele | 6-2,6-1 |
| Challenger Cleveland | 2023/01/30 15:00 | Bradley Klahn v Ryan Harrison | 3-6,6-7 |