Stadium: Court 2 Round: 45 Ground: Hardcourt outdoor
| Challenger Taipei Qual | 2018/04/09 03:00 | Roelofse, Ruan v Grills, Jacob | 6-4,2-6,7-6 |
| Challenger Aptos | 2018/08/04 17:20 | Roelofse, Ruan v Alex Rybakov | 3-6,6-7 |
| Challenger Lexington Qual | 2018/07/30 16:00 | Alex Rybakov v Roelofse, Ruan | 7-5,7-6 |
| Challenger Lexington Qual | 2018/07/29 16:45 | Hussey, Austin v Roelofse, Ruan | 1-6,1-6 |
| Challenger Lexington Qual | 2018/07/28 18:55 | Roelofse, Ruan v Takeuchi, Kento (1987) | 6-4,6-4 |
| Challenger Binghamton Qual | 2018/07/21 17:20 | Roelofse, Ruan v Hiltzik, Jared | 5-7,4-6 |
| Challenger Puerto Vallarta Qual | 2018/04/28 19:25 | Olivares, Jose v Roelofse, Ruan | 6-3,7-5 |
| Challenger - Taipei | 2018/04/10 06:50 | Chen, Ti v Roelofse, Ruan | 7-6,6-3 |
| Challenger Taipei Qual | 2018/04/09 03:00 | Roelofse, Ruan v Grills, Jacob | 6-4,2-6,7-6 |
| Challenger Aptos | 2018/08/04 16:00 | Craig, Henry v Grills, Jacob | 6-2,2-6,6-1 |
| ATP Los Cabos Qual | 2018/07/28 23:00 | Grills, Jacob v Aleksandar Vukic | 6-3,2-6,3-6 |
| Challenger Granby | 2018/07/24 17:05 | Grills, Jacob v Stefano Napolitano | 1-6,6-7 |
| Challenger Granby Qual | 2018/07/23 16:00 | Lucas Miedler v Grills, Jacob | 2-6,6-2,7-6 |
| Challenger Granby Qual | 2018/07/22 21:30 | Grills, Jacob v Shintaro Imai | 6-4,6-1 |
| Challenger Granby Qual | 2018/07/21 14:00 | Gervais, Washi v Grills, Jacob | 4-6,2-6 |
| Gatineau, Canada | 2018/07/19 15:00 | Grills, Jacob v Soeda, Go | 6-2,1-6,4-6 |
| Gatineau, Canada | 2018/07/17 17:15 | Grills, Jacob v Sarkissian, Alexander | 6-3,7-6 |