Stadium: Center Court Round: 46
| Challenger Winnetka Qual | 2018/07/07 19:35 | Osgar O'Hoisin v Emmett Ward | 6-2,2-6,6-3 |
| ITF USA F18 | 2018/06/27 18:00 | Osgar O'Hoisin v Sean Sculley | 3-6,0-6 |
| ITF USA F15 Qual | 2018/06/17 14:00 | Gage Brymer v Osgar O'Hoisin | 6-4,6-7,7-6 |
| ITF USA F15 Qual | 2018/06/16 13:00 | Collin Thomson v Osgar O'Hoisin | 4-6,5-7 |
| ITF Ireland F2 | 2017/07/26 12:55 | Osgar O'Hoisin v Michal Konecny | 6-4,3-6,6-7 |
| ITF Ireland F2 | 2017/07/25 11:15 | Sean Collins v Osgar O'Hoisin | 2-6,3-6 |
| ITF Ireland F1 | 2017/07/20 15:00 | Remi Boutillier v Osgar O'Hoisin | 7-6,7-5 |
| ITF Ireland F1 | 2017/07/18 10:40 | Osgar O'Hoisin v Alexander Jhun | 4-6,6-2,6-3 |
| Challenger Winnetka Qual | 2018/07/07 20:55 | Aleksandar Kovacevic v Alex Rybakov | 1-6,7-6,2-6 |
| ITF USA F16 | 2018/06/24 14:30 | Markos Kalovelonis v Alex Rybakov | 1-6,6-7 |
| ITF USA F16 | 2018/06/23 14:30 | Alex Rybakov v Andres Andrade | 6-1,6-4 |
| ITF USA F16 | 2018/06/22 21:05 | Mateo Nicolas Martinez v Alex Rybakov | 6-4,1-6,2-6 |
| ITF USA F16 | 2018/06/21 17:00 | Kelsey Stevenson v Alex Rybakov | 4-6,1-6 |
| ITF USA F16 | 2018/06/20 19:45 | David Souto v Alex Rybakov | 4-6,1-6 |
| ITF USA F14 | 2018/06/16 17:10 | Lucas Gomez v Alex Rybakov | 3-6,2-6 |
| ITF USA F14 | 2018/06/15 16:50 | Mateo Nicolas Martinez v Alex Rybakov | 7-6,6-7,3-6 |