Stadium: Court 1 Round: 28 Ground: Hardcourt indoor
| ITF M15 Los Angeles | 2022/06/29 18:00 | Ethan Quinn v Patrick Kypson | 3-6,2-6 |
| Challenger Champaign | 2023/11/17 23:00 | Aleksandar Kovacevic v Patrick Kypson | 6-7,6-4,3-6 |
| Challenger Champaign | 2023/11/16 00:35 | Kenta Miyoshi v Patrick Kypson | 3-6,1-6 |
| Challenger Champaign | 2023/11/14 18:35 | Mark Whitehouse v Patrick Kypson | 1-6,6-7 |
| Challenger Knoxville | 2023/11/07 15:00 | Denis Kudla v Patrick Kypson | 6-7,6-3,6-4 |
| Challenger Charlottesville | 2023/11/04 17:30 | Beibit Zhukayev v Patrick Kypson | 6-4,7-6 |
| Challenger Charlottesville | 2023/11/03 16:00 | Patrick Kypson v Brandon Holt | 6-1,6-4 |
| Challenger Charlottesville | 2023/11/01 18:20 | Denis Kudla v Patrick Kypson | 1-6,3-6 |
| Challenger Charlottesville | 2023/10/30 19:30 | Patrick Kypson v Gabriel Debru | 6-4,7-5 |
| Challenger Champaign | 2023/11/17 18:55 | Ethan Quinn v Nino Serdarusic | 6-3,6-3 |
| Challenger Champaign | 2023/11/15 17:00 | Ethan Quinn v Strong Kirchheimer | 6-1,6-4 |
| Challenger Champaign | 2023/11/14 16:00 | Emilio Nava v Ethan Quinn | 3-6,2-6 |
| Challenger Knoxville | 2023/11/07 15:00 | Tennys Sandgren v Ethan Quinn | 4-6,7-6,7-6 |
| Challenger Charlottesville | 2023/11/04 19:25 | Aidan Mayo v Ethan Quinn | 3-6,6-4,6-3 |
| Challenger Charlottesville | 2023/11/03 22:00 | Benoit Paire v Ethan Quinn | 6-7,2-6 |
| Challenger Charlottesville | 2023/11/02 16:00 | Ethan Quinn v Emilio Nava | 6-3,6-1 |
| Challenger Charlottesville | 2023/10/31 14:00 | Ethan Quinn v Mitchell Krueger | 3-6,7-6,6-4 |