Stadium: Court 4 Round: 25 Ground: Hardcourt indoor
| 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 |
| Challenger Columbus | 2022/09/20 14:00 | Ryan Harrison v Paul Jubb | 6-7,4-6 |
| Challenger Cary | 2022/09/16 01:45 | Ryan Harrison v Nick Chappell | 4-6,6-4,2-6 |
| Challenger Cary | 2022/09/14 00:10 | Aleksandar Vukic v Ryan Harrison | 6-7,6-7 |
| Challenger Cary | 2022/09/12 16:00 | Ezekiel Clark v Ryan Harrison | 2-6,6-7 |
| Challenger Cary | 2022/09/11 15:00 | Pedro Rodenas v Ryan Harrison | 3-6,4-6 |
| Challenger Chicago | 2022/08/11 19:10 | Ryan Harrison v Jordan Thompson | 3-6,3-6 |
| Challenger Cleveland | 2023/01/30 15:00 | Jaimee Floyd Angele v Roy Smith | 6-4,6-7,6-4 |
| Challenger Cleveland | 2023/01/29 15:00 | Jaimee Floyd Angele v Evan King | 6-2,6-3 |
| ITF M25 Wesley Chapel | 2023/01/26 15:00 | Jaimee Floyd Angele v Alfredo Perez | 4-6,4-6 |
| ITF M25 Wesley Chapel | 2023/01/25 18:35 | Leo Vithoontien v Jaimee Floyd Angele | 3-6,4-6 |
| ITF M25 Doha | 2023/01/19 12:00 | Bogdan Bobrov v Jaimee Floyd Angele | 3-6,6-3,7-5 |
| ITF M25 Doha | 2023/01/18 13:25 | Jaimee Floyd Angele v Mukund Sasikumar | 6-2,6-4 |
| ITF M25 Doha | 2023/01/17 16:30 | Jaimee Floyd Angele v Deney Wassermann | 7-6,6-7,7-6 |
| ITF M15 Doha | 2023/01/11 12:00 | Kristjan Tamm v Jaimee Floyd Angele | 6-3,6-2 |