Stadium: Court 5N Round: 26 Ground: Hardcourt outdoor
| ITF - M15 Champaign | 2023/09/13 23:15 | Oliver Okonkwo v Facundo Yunis | 6-1,4-6,6-1 |
| ITF - M25 Decatur | 2023/08/03 13:55 | Shunsuke Mitsui v Oliver Okonkwo | 7-6,6-4 |
| ITF - M25 Decatur | 2023/08/01 16:05 | Oliver Okonkwo v Semen Pankin | 6-2,1-6,10-8 |
| ITF - M25 Edwardsville | 2023/07/24 14:00 | Kenta Miyoshi v Oliver Okonkwo | 6-3,6-4 |
| ITF - M25 Champaign | 2023/07/18 14:55 | Perry Gregg v Oliver Okonkwo | 3-6,6-2,10-7 |
| ITF - M15 South Bend | 2023/06/21 17:05 | Adhithya Ganesan v Oliver Okonkwo | 6-0,6-3 |
| ITF - M15 South Bend | 2023/06/20 15:00 | John Bernard v Oliver Okonkwo | 2-6,4-6 |
| ITF - M15 South Bend | 2023/06/19 14:00 | Oliver Okonkwo v Sean Daryabeigi | 3-6,6-3,13-11 |
| ITF - M15 Champaign | 2023/09/13 15:00 | Patrick Maloney v A.J Catanzariti | 1-6,7-6,6-3 |
| ITF - M15 Pittsburgh | 2023/07/27 18:05 | Samir Banerjee v Patrick Maloney | 6-3,2-6,6-2 |
| ITF - M15 Pittsburgh | 2023/07/26 13:50 | Patrick Maloney v Jacob Brumm | 6-1,6-4 |
| ITF - M15 Rochester | 2023/07/19 18:15 | Patrick Maloney v Henrik Wiersholm | 6-3,4-6,5-7 |
| ITF - M25 Dallas | 2023/07/14 15:55 | Blake Ellis v Patrick Maloney | 6-3,3-6,7-5 |
| ITF - M25 Dallas | 2023/07/12 18:50 | Pranav Kumar v Patrick Maloney | 6-4,2-6,1-6 |
| Challenger - Bloomfield Hills | 2023/07/03 14:15 | Patrick Maloney v Colin Sinclair | 7-6,6-7,3-6 |
| Challenger - Knoxville | 2022/11/07 15:00 | Strong Kirchheimer v Patrick Maloney | 7-6,6-4 |