Stadium: Court 5 Round: 45
| Challenger Winnetka Qual | 2018/07/07 15:00 | Sam Riffice v Collin Altamirano | 6-7,6-3,4-6 |
| ITF USA F17 | 2018/07/01 15:30 | Marc-Andrea Huesler v Sam Riffice | 6-4,6-2 |
| ITF USA F17 | 2018/06/30 15:00 | Sam Riffice v Emil Reinberg | 6-0,6-3 |
| ITF USA F17 | 2018/06/29 18:00 | Sam Riffice v Mikael Torpegaard | 7-5,6-1 |
| ITF USA F17 | 2018/06/28 15:00 | Henry Craig v Sam Riffice | 4-6,6-2,2-6 |
| ITF USA F15 | 2018/06/22 16:00 | Sam Riffice v Henry Craig | 5-7,5-7 |
| ITF USA F15 | 2018/06/21 15:45 | Ryan Peniston v Sam Riffice | 1-6,5-7 |
| ITF USA F15 | 2018/06/20 14:00 | Sam Riffice v Jacob Dunbar | 6-3,6-4 |
| Challenger Winnipeg Qual | 2018/07/08 19:25 | Alexios Halebian v Marc-Andrea Huesler | 6-7,4-6 |
| ITF Canada F5 | 2018/07/05 18:20 | Alexios Halebian v David Volfson | 4-6,6-7 |
| ITF Canada F5 | 2018/07/04 23:30 | Alexios Halebian v Riaan Du Toit | 6-1,7-6 |
| ITF Canada F4 | 2018/06/26 17:00 | Alexios Halebian v Brandon Holt | 1-6,6-4,4-6 |
| ITF Canada F3 | 2018/06/21 16:00 | Juan Carlos Aguilar v Alexios Halebian | 6-4,6-3 |
| ITF Canada F3 | 2018/06/20 17:30 | Samuel Shropshire v Alexios Halebian | 6-4,3-6,0-6 |
| ITF USA F13 | 2018/06/13 19:15 | Petros Chrysochos v Alexios Halebian | 6-2,6-4 |
| ITF Vietnam F3 | 2018/05/17 03:00 | Cheng-Yu Yu v Alexios Halebian | 6-4,6-2 |