Stadium: Court N5 Round: 25 Ground: Clay
| ITF USA F20 Qual | 2018/07/23 16:50 | Perez, Alfredo v Kessler, Mcclain | 6-3,3-6,6-7 |
| ITF USA F20 Qual | 2018/07/21 15:00 | Kessler, Mcclain v Seeberger, Matt | 6-2,6-3 |
| ITF USA F19B Qual | 2018/07/15 15:00 | Rollins, Pierce v Kessler, Mcclain | 6-3,7-5 |
| 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 F16 | 2018/06/21 19:50 | Ross, Gianni v Mcnally, John | 6-4,6-2 |
| ITF USA F16 | 2018/06/20 19:30 | Mcnally, John v Torre, Eduardo Agustin | 6-4,6-3 |
| ITF USA F16 | 2018/06/18 17:00 | Mcnally, John v Every, Michael-John | 6-3,6-4 |
| ITF USA F16 | 2018/06/17 17:00 | Mcnally, John v Naser, Javier | 6-4,6-1 |
| ITF USA F16 | 2018/06/16 19:00 | Mcnally, John v Drew Van Orderlain | 7-6,6-3 |
| ITF USA F14 | 2018/06/14 18:50 | Torre, Eduardo Agustin v Mcnally, John | 6-0,7-5 |
| ITF USA F14 | 2018/06/13 18:00 | Mcnally, John v Isaiah Strode | 6-2,6-4 |
| ITF USA F38 | 2017/11/22 17:00 | Torpegaard, Mikael v Mcnally, John | 6-3,6-1 |