Stadium: Central Round: 166 Ground: Hardcourt outdoor
| ITF Canada F5 | 2018/07/05 20:45 | Boulais, Justin v Grills, Jacob | 7-5,1-6,3-6 |
| Challenger Winnipeg | 2019/07/10 15:00 | Grills, Jacob v Shintaro Imai | 7-6,6-7,0-6 |
| Parma II, Italy | 2019/06/20 08:00 | Grills, Jacob v Jacopo Berrettini | 1-6,4-6 |
| Parma II, Italy | 2019/06/18 08:00 | Taro Daniel v Grills, Jacob | 6-4,3-6,4-6 |
| Parma II, Italy | 2019/06/17 09:10 | Heyman, Christopher v Grills, Jacob | 6-7,1-6 |
| Kaltenkirchen, Singles Qualifying M-ITF-GER-05A | 2019/06/12 13:45 | Grills, Jacob v Stebe, Cedrik-Marcel | 4-6,6-4,1-6 |
| Kaltenkirchen, Singles Qualifying M-ITF-GER-05A | 2019/06/11 17:25 | Grills, Jacob v Matheus P De Almeida | 5-7,7-6,7-6 |
| Poznan, Poland | 2019/06/03 09:55 | Grills, Jacob v Zdenek Kolar | 1-6,3-6 |
| ITF M25 Most | 2019/05/30 10:25 | Krstev, Ondrej v Grills, Jacob | 2-6,6-4,6-3 |
| Challenger Winnipeg | 2019/07/11 18:20 | Boulais, Justin v Schnur, Brayden | 4-6,7-6,3-6 |
| Challenger Winnipeg | 2019/07/10 20:00 | Kaichi Uchida v Boulais, Justin | 6-3,3-6,3-6 |
| Challenger Winnipeg | 2019/07/08 16:00 | Issei Okamura v Boulais, Justin | 2-6,5-7 |
| ITF M15 Pittsburgh | 2019/07/02 14:00 | Boulais, Justin v A.J Catanzariti | 2-6,6-4,4-6 |
| Orlando, Singles Qualifying M-ITF-USA-17A | 2019/06/19 19:05 | Boulais, Justin v Rodriguez-Pace, Ricardo | 4-6,5-7 |
| Challenger Columbus | 2019/06/10 18:55 | Alexis Galarneau v Boulais, Justin | 6-7,6-4,6-0 |
| ITF - M15 Antalya | 2019/04/03 08:50 | Boulais, Justin v Avidzba, Alen | 6-7,1-6 |
| ITF - M15 Antalya | 2019/03/27 07:00 | Boulais, Justin v Grigoriy Lomakin | 6-7,1-6 |