Stadium: Court 4 Round: 62
| ITF USA F19 Qual | 2018/07/02 14:00 | Stalder, Reese v Rollins, Pierce | 6-3,7-6 |
| ITF USA F17 Qual | 2018/06/24 18:30 | Boyer, Dusty H v Rollins, Pierce | 6-4,6-4 |
| ITF USA F21 Qual | 2017/06/26 16:00 | Spec, Matic v Rollins, Pierce | 6-3,6-4 |
| ITF USA F21 Qual | 2017/06/25 14:00 | Rollins, Pierce v Filipovic, Igor | 6-1,6-1 |
| ITF USA F21 Qual | 2017/06/24 16:30 | Rollins, Pierce v Landa Catan, Pablo | 7-6,6-2 |
| Challenger Winnetka Qual | 2018/07/07 18:05 | Strong Kirchheimer v Kessler, Mcclain | 6-1,7-5 |
| ITF USA F19 | 2018/07/04 13:30 | Dunbar, Jacob v Kessler, Mcclain | 6-1,6-0 |
| ITF USA F19 Qual | 2018/07/02 16:40 | Kessler, Mcclain v Maxime Cressy | 6-4,6-7,7-6 |
| ITF USA F19 Qual | 2018/07/01 15:00 | Kessler, Mcclain v Pickens, A.trice | 6-2,7-5 |
| ITF USA F13 Qual | 2018/06/10 14:00 | Hamilton, Grey v Kessler, Mcclain | 7-6,6-4 |
| ITF USA F13 Qual | 2018/06/09 13:00 | Arimilli, Nevin v Kessler, Mcclain | 6-3,2-6,2-6 |
| ITF USA F4 | 2018/01/14 18:00 | Ore, I. A. v Kessler, Mcclain | 6-0,6-2 |
| ITF USA F24 Qual | 2017/07/15 14:00 | Kessler, Mcclain v Seidman, Jason | 6-3,3-6,6-7 |