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