stadio: Stadium Court Round: 14 Ground: Clay
| ITF M15 Sunrise | 2023/04/13 15:00 | Kaylan Bigun v Kyle Kang | 5-7,4-6 |
| ITF M15 Sunrise | 2023/04/11 21:00 | Jesse Flores v Kaylan Bigun | 1-6,4-6 |
| ITF M15 Naples | 2023/02/28 16:30 | Jonathan Mridha v Kaylan Bigun | 6-2,6-0 |
| ITF M15 Antalya | 2022/10/27 07:00 | Kaylan Bigun v Peter Heller | 2-6,2-6 |
| ITF M15 Antalya | 2022/10/25 10:20 | Kaylan Bigun v Denis Klok | 3-6,6-4,6-0 |
| ITF M15 Antalya | 2022/10/19 09:35 | Yassine Dlimi v Kaylan Bigun | 6-1,6-2 |
| ITF M15 Memphis | 2022/08/17 21:00 | Tennys Sandgren v Kaylan Bigun | 6-4,6-1 |
| ITF M15 Cancun | 2022/07/12 17:00 | Kaylan Bigun v Fernando Yamacita | 5-7,2-6 |
| 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 (Georgia) | 2023/02/22 16:35 | Ryan Harrison v Elmar Ejupovic | 6-3,6-7,2-6 |
| Challenger Rome (Georgia) | 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 |
| Challenger Cleveland | 2023/01/29 18:50 | Nico Mostardi v Ryan Harrison | 3-6,4-6 |