| ITF - M25 - Edwardsville | 2019/08/05 14:00 | Jason Kerst v McClain Kessler | 6-2,7-6 |
| ITF - M25 - Decatur | 2019/07/31 16:40 | Christian Langmo v McClain Kessler | 6-4,6-4 |
| ITF - M25 - Decatur | 2019/07/30 15:00 | McClain Kessler v Ishaan Ravichander | 6-2,6-4 |
| ITF - M25 - Champaign | 2019/07/24 21:05 | Kareem Allaf v McClain Kessler | 6-4,6-2 |
| ITF - M25 - Champaign | 2019/07/23 16:50 | Vuk Budic v McClain Kessler | 1-6,6-3,9-11 |
| ITF - M15 - Rochester | 2019/06/24 17:00 | Jordan Benjamin v McClain Kessler | 1-6,6-3,10-7 |
| ITF - M15 - Orlando | 2019/06/18 13:00 | McClain Kessler v Logan Zapp | 5-7,2-6 |
| ITF - M25 - Wichita | 2019/06/11 16:45 | Pierce Rollins v McClain Kessler | 6-2,3-6,10-7 |