Stadium: Court 4 Round: 25 Ground: Hardcourt outdoor
| Challenger Lexington Qual | 2018/07/29 16:30 | Alex Rybakov v Strong Kirchheimer | 4-6,7-5,6-3 |
| Challenger Lexington Qual | 2018/07/28 17:40 | Nick Chappell v Strong Kirchheimer | 6-4,2-6,3-6 |
| ITF USA F20 Qual | 2018/07/21 15:00 | Strong Kirchheimer v Kaptan Kaster | 6-2,6-2 |
| ITF USA F19B | 2018/07/19 17:00 | Kareem Allaf v Strong Kirchheimer | 6-3,6-4 |
| ITF USA F19B | 2018/07/18 17:00 | Piotr Smietana v Strong Kirchheimer | 1-6,0-6 |
| Challenger Winnetka Qual | 2018/07/08 15:00 | Luke Saville v Strong Kirchheimer | 6-2,6-4 |
| Challenger Winnetka Qual | 2018/07/07 18:05 | Strong Kirchheimer v McClain Kessler | 6-1,7-5 |
| ITF USA F18 | 2018/06/29 15:30 | Jordi Arconada v Strong Kirchheimer | 7-6,5-7,6-3 |
| ITF USA F20 | 2018/07/24 18:45 | Brian Shi v Santiago Rodriguez Taverna | 4-6,2-6 |
| ITF USA F19B Qual | 2018/07/16 15:00 | Brian Shi v Alexander Brown | 6-3,1-6,4-6 |
| ITF USA F19B Qual | 2018/07/15 15:00 | Brian Shi v Carson Haskins | 6-4,1-6,6-3 |
| ITF Canada F4 Qual | 2018/06/24 17:00 | Brian Shi v Taha Baadi | 4-6,5-7 |
| ITF USA F13 | 2018/06/15 15:00 | Karue Sell v Brian Shi | 3-6,6-3,6-4 |
| ITF USA F13 | 2018/06/14 18:00 | Brian Shi v Felipe Mantilla | 6-4,2-6,6-4 |
| ITF USA F13 | 2018/06/13 18:55 | Skander Mansouri v Brian Shi | 2-6,6-7 |
| ITF USA F13 Qual | 2018/06/11 18:05 | Brian Shi v Drew Van Orderlain | 6-3,6-2 |