Stadion: Court 1 Round: 19 Ground: Hardcourt indoor
| Challenger - Champaign | 2023/11/12 23:10 | Christian Harrison v Oliver Okonkwo | 4-6,6-3,6-7 |
| ITF - M15 - Champaign | 2023/09/14 19:35 | Oliver Okonkwo v Patrick Maloney | 3-6,1-6 |
| 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 |
| Challenger - Champaign | 2023/11/13 00:20 | Hunter Heck v Ezekiel Clark | 7-5,6-0 |
| ITF - M15 - Champaign | 2023/09/15 17:40 | William Grant v Hunter Heck | 7-6,6-1 |
| ITF - M15 - Champaign | 2023/09/14 15:00 | Hunter Heck v Axel Nefve | 6-2,6-4 |
| ITF - M15 - Champaign | 2023/09/12 20:30 | Hunter Heck v Andrew Fenty | 7-5,7-6 |
| ITF - M25 - Decatur | 2023/08/05 17:50 | Cash Hanzlik v Hunter Heck | 6-2,6-1 |
| ITF - M25 - Decatur | 2023/08/04 14:00 | Hunter Heck v Ezekiel Clark | 6-1,6-0 |
| ITF - M25 - Decatur | 2023/08/03 19:50 | Shunsuke Mitsui v Hunter Heck | 0-6,2-6 |
| ITF - M25 - Edwardsville | 2023/07/26 18:35 | Hunter Heck v Michael Zheng | 6-4,4-6,2-6 |