| UTR Pro Florida | 2023/08/03 16:45 | Matthew Pitts v Dakotah Bobo | 7-5,7-6 |
| UTR Pro Florida | 2023/08/02 16:30 | Elias Shokry v Dakotah Bobo | 6-4,6-4 |
| UTR Pro Florida | 2023/08/01 16:04 | Liam Oliver Toroman v Dakotah Bobo | 0-6,2-5 |
| UTR Pro Florida | 2023/07/30 18:07 | Dakotah Bobo v Jerry Barton | 1-6,4-6 |
| UTR Pro Florida | 2023/06/23 15:06 | Dakotah Bobo v Lucas Silva | 1-6,1-6 |
| UTR Pro Florida | 2023/05/14 17:00 | Jibril Nettles v Dakotah Bobo | 6-7,1-6 |
| UTR Pro Florida | 2023/05/13 19:44 | Dakotah Bobo v Andre Szilvassy | 6-3,6-2 |
| UTR Pro Florida | 2023/05/12 21:00 | Dmitry Popko v Dakotah Bobo | 6-4,6-3 |
| UTR Pro Ann Arbor | 2023/07/30 13:00 | Jacob Bickersteth v Sebastian Sec | 7-5,1-6,2-6 |
| UTR Pro Ann Arbor | 2023/07/29 14:57 | Jacob Bickersteth v Tanapatt Nirundorn | 7-6,6-3 |
| UTR Pro Ann Arbor | 2023/07/28 14:00 | Nate Bonetto v Jacob Bickersteth | 4-6,3-6 |
| UTR Pro Ann Arbor | 2023/07/27 20:21 | Max Bengtsson v Jacob Bickersteth | 2-6,4-6 |
| UTR Pro Ann Arbor | 2023/07/26 13:51 | Ekansh Kumar v Jacob Bickersteth | 6-7,0-6 |
| UTR Pro Ann Arbor | 2023/07/24 16:00 | Douglas Yaffa v Jacob Bickersteth | 2-6,6-7 |
| ITF M15 South Bend | 2023/06/21 16:30 | Strong Kirchheimer v Jacob Bickersteth | 6-2,6-2 |
| UTR Pro Tennis Series California | 2022/08/06 17:00 | Jacob Bickersteth v Peter Makk | 3-6,2-6 |