Stadium: Court 1 Round: 29 Ground: Hardcourt indoor
| Challenger Savannah | 2023/04/24 18:45 | Alex Michelsen v Kypson, Patrick | 6-4,3-6,6-7 |
| Challenger Champaign | 2023/11/18 21:45 | Kypson, Patrick v Quinn, Ethan | 6-4,6-2 |
| Challenger Champaign | 2023/11/17 23:00 | 코바세비치, 알렉산달 v Kypson, Patrick | 6-7,6-4,3-6 |
| Challenger Champaign | 2023/11/16 00:35 | Miyoshi, Kenta v Kypson, Patrick | 3-6,1-6 |
| Challenger Champaign | 2023/11/14 18:35 | 화이트하우스, 마르크 v Kypson, Patrick | 1-6,6-7 |
| Challenger Knoxville | 2023/11/07 15:00 | 쿠들라, 다니스 v Kypson, Patrick | 6-7,6-3,6-4 |
| Challenger Charlottesville | 2023/11/04 17:30 | 주카예브, 베이비트 v Kypson, Patrick | 6-4,7-6 |
| Challenger Charlottesville | 2023/11/03 16:00 | Kypson, Patrick v 홀트, 브란던 | 6-1,6-4 |
| Challenger Charlottesville | 2023/11/01 18:20 | 쿠들라, 다니스 v Kypson, Patrick | 1-6,3-6 |
| Challenger Champaign | 2023/11/18 19:35 | Droguet, Titouan v Alex Michelsen | 6-2,4-6,3-6 |
| Challenger Champaign | 2023/11/17 17:00 | 담, 마르틴 v Alex Michelsen | 1-6,6-1,4-6 |
| Challenger Champaign | 2023/11/16 18:20 | 판세로, 세바스티안 v Alex Michelsen | 3-6,2-6 |
| Challenger Champaign | 2023/11/15 01:25 | 토미크, 베르날다 v Alex Michelsen | 4-6,0-6 |
| Challenger Knoxville | 2023/11/12 18:00 | 쿠들라, 다니스 v Alex Michelsen | 5-7,6-4,2-6 |
| Challenger Knoxville | 2023/11/11 18:25 | Alex Michelsen v 산드그렌, 테니스 | 6-2,2-6,6-4 |
| Challenger Knoxville | 2023/11/10 19:05 | Nishesh Basavareddy v Alex Michelsen | 3-6,3-6 |
| Challenger Knoxville | 2023/11/08 17:50 | Gabriel Debru v Alex Michelsen | 3-6,6-3,4-6 |