Stadium: Court 9 Round: 25 Ground: Clay
| ITF M25 Wichita | 2021/06/13 17:00 | Govind Nanda v Patrick Kypson | 7-6,6-2 |
| ITF M25 Wichita | 2021/06/12 15:00 | Patrick Kypson v Felix Corwin | 6-3,6-2 |
| ITF M25 Wichita | 2021/06/11 15:00 | Zachary Svajda v Patrick Kypson | 7-6,1-6,6-7 |
| ITF M25 Wichita | 2021/06/10 15:00 | Patrick Kypson v Alexander Sarkissian | 6-2,4-6,6-3 |
| ITF M25 Wichita | 2021/06/09 19:20 | Patrick Kypson v Gabriel Diallo | 6-4,6-4 |
| Challenger Little Rock | 2021/05/30 16:15 | Patrick Kypson v Dayne Kelly | 6-4,3-6,2-6 |
| ITF M25 Pensacola | 2021/05/22 15:55 | Patrick Kypson v Nicolas Kicker | 6-7,0-6 |
| ITF M25 Pensacola | 2021/05/21 14:30 | Alejandro Gonzalez v Patrick Kypson | 4-6,0-6 |
| ITF M25 Weston | 2021/06/29 23:15 | Jesse Witten v Kiranpal Pannu | 6-4,6-2 |
| ITF M25 Weston | 2021/06/29 20:45 | Peter Bertran v Jesse Witten | 7-5,2-6,8-10 |
| ITF M25 Naples | 2021/02/24 14:55 | Jesse Witten v Zane Khan | 2-6,5-7 |
| UTR Pro Tennis Series Florida | 2020/12/16 18:26 | Felix Corwin v Jesse Witten | 6-2,6-4 |
| UTR Pro Tennis Series Florida | 2020/12/15 20:00 | Connor Krug v Jesse Witten | 6-2,1-6,4-6 |
| UTR Pro Tennis Series Florida | 2020/12/15 00:00 | Jesse Witten v Anze Arh | 6-3,4-6,5-1 |
| ITF M25 Naples | 2020/02/11 15:00 | Daniel Dutra Da Silva v Jesse Witten | 6-3,6-3 |
| ITF M25 Naples | 2020/02/10 15:30 | Jose Daniel Bendeck v Jesse Witten | 2-6,5-7 |