| Challenger de Charlottesville | 11/03 16:00 | 27 | [254] Patrick Kypson v Brandon Holt [285] | 6-1,6-4 | |
| Challenger de Charlottesville | 11/01 18:20 | 26 | [180] Denis Kudla v Patrick Kypson [254] | 1-6,3-6 | |
| Challenger de Charlottesville | 10/30 19:30 | 25 | [254] Patrick Kypson v Gabriel Debru [322] | 6-4,7-5 | |
| Challenger de Fairfield | 10/09 20:45 | 25 | [256] Patrick Kypson v Aidan Mayo [387] | 6-3,6-7,6-7 | |
| Challenger Tiburón | 10/02 22:35 | 25 | [176] Alexis Galarneau v Patrick Kypson [249] | 7-6,6-4 | |
| Challenger de Charleston | 09/27 16:10 | 25 | [249] Patrick Kypson v Ryan Peniston [197] | 2-6,4-6 | |
| Challenger de Cary | 09/16 19:00 | 28 | [82] Rinky Hijikata v Patrick Kypson [271] | 6-4,6-2 | |
| Challenger de Cary | 09/15 23:00 | 27 | [271] Patrick Kypson v Tennys Sandgren [196] | 7-6,6-3 | |
| Challenger de Cary | 09/14 23:00 | 26 | [203] Adam Walton v Patrick Kypson [271] | 5-7,3-6 | |
| Challenger de Cary | 09/13 16:00 | 25 | [271] Patrick Kypson v Michael Geerts [285] | 6-1,6-3 | |
| US Open | 08/24 14:00 | 15 | [274] Patrick Kypson v Juncheng Shang [160] | 4-6,6-7 | |
| US Open | 08/22 17:50 | 14 | [102] Jurij Rodionov v Patrick Kypson [274] | 4-6,4-6 | |
| Challenger de Cary | 08/12 21:25 | 28 | [297] Patrick Kypson v Nicolás Moreno de Alboran [149] | 7-6,3-6,1-6 | |
| Challenger de Cary | 08/11 21:30 | 27 | [297] Patrick Kypson v Tung-Lin Wu [205] | 6-3,7-6 | |
| Challenger de Cary | 08/10 21:45 | 26 | [206] Seong Chan Hong v Patrick Kypson [297] | 4-6,4-6 | |
| Challenger de Cary | 08/09 00:15 | 25 | Keegan Smith v Patrick Kypson | 3-6,2-6 | |
| ATP Los Cabos | 07/30 01:00 | 14 | Keegan Smith v Patrick Kypson | 6-3,6-7,6-2 | |
| Challenger de Granby | 07/18 16:50 | 25 | [88] Thanasi Kokkinakis v Patrick Kypson [275] | 6-2,6-7,6-4 | |
| Challenger de Granby | 07/17 14:00 | 19 | [275] Patrick Kypson v Nathan Ponwith [396] | 6-3,7-5 | |
| Challenger de Granby | 07/16 19:20 | 14 | [271] Patrick Kypson v Tristan McCormick [495] | 7-6,6-2 | |
| Challenger de Medellín | 07/01 18:00 | 29 | [372] Benjamin Lock v Patrick Kypson [330] | 3-6,3-6 | |
| Challenger de Medellín | 06/30 18:00 | 28 | [330] Patrick Kypson v Eduardo Ribeiro [344] | 6-4,7-6 | |
| Challenger de Medellín | 06/29 15:00 | 27 | [330] Patrick Kypson v Matias Soto [292] | 6-3,6-2 | |
| Challenger de Medellín | 06/28 15:00 | 26 | [330] Patrick Kypson v Gonzalo Lama [427] | 7-6,6-1 | |
| Challenger de Medellín | 06/27 16:40 | 25 | [330] Patrick Kypson v Matias Franco Descotte [426] | 6-4,6-3 | |
| Challenger de Cali | 06/20 18:15 | 25 | [466] Pedro Sakamoto v Patrick Kypson [328] | 7-5,6-3 | |
| Challenger de Palmas del Mar | 06/13 15:00 | 25 | [329] Patrick Kypson v Alexis Galarneau [224] | 3-6,0-6 | |
| Challenger de Tyler | 06/04 17:25 | 14 | [329] Patrick Kypson v Rubin Statham [467] | 6-7,6-4,6-7 | |
| Open de Francia | 05/28 09:00 | 23 | [329] Patrick Kypson v Radu Albot [113] | 3-6,2-6,6-4,1-6 | |
| Challenger de Savannah | 04/29 17:30 | 28 | [378] Patrick Kypson v Facundo D Acosta [160] | 3-6,6-4,4-6 |