Stadion: Court 1 Round: 29 Ground: Hardcourt indoor
| Challenger - Savannah | 2023/04/24 18:45 | Alex Michelsen v Patrick Kypson | 6-4,3-6,6-7 |
| Challenger - Champaign | 2023/11/18 21:45 | Patrick Kypson v Ethan Quinn | 6-4,6-2 |
| 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 - Champaign | 2023/11/18 19:35 | Titouan Droguet v Alex Michelsen | 6-2,4-6,3-6 |
| Challenger - Champaign | 2023/11/17 17:00 | Martin Damm v Alex Michelsen | 1-6,6-1,4-6 |
| Challenger - Champaign | 2023/11/16 18:20 | Sebastian Fanselow v Alex Michelsen | 3-6,2-6 |
| Challenger - Champaign | 2023/11/15 01:25 | Bernard Tomic v Alex Michelsen | 4-6,0-6 |
| Challenger - Knoxville | 2023/11/12 18:00 | Denis Kudla v Alex Michelsen | 5-7,6-4,2-6 |
| Challenger - Knoxville | 2023/11/11 18:25 | Alex Michelsen v Tennys Sandgren | 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 |