Stadium: Court 3 Round: 24 Ground: Hardcourt outdoor
| Challenger Granby Qual | 2018/07/22 21:30 | Jacob Grills v Shintaro Imai | 6-4,6-1 |
| ITF Japan F5 | 2018/04/02 03:10 | Shintaro Imai v Jacob Grills | 6-1,6-1 |
| ITF Hong Kong F3 | 2017/07/08 01:30 | Jacob Grills v Shintaro Imai | 6-7,3-6 |
| 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 |
| ITF M25 Most | 2019/05/29 08:00 | Jiri Barnat v Jacob Grills | 3-6,2-6 |
| ITF M25 Hengyang | 2019/06/21 02:00 | Shintaro Imai v Harry Bourchier | 4-6,3-6 |
| ITF M25 Hengyang | 2019/06/20 03:40 | Shintaro Imai v Aliaksandr Liaonenka | 7-5,6-1 |
| ITF M25 Hengyang | 2019/06/19 04:35 | Shintaro Imai v Li-Wei Tan | 6-4,6-0 |
| ITF M25 Hong Kong | 2019/06/16 02:00 | Agustin Velotti v Shintaro Imai | 6-3,6-3 |
| ITF M25 Hong Kong | 2019/06/15 03:00 | Shintaro Imai v Chun Hsin Tseng | 6-2,6-2 |
| ITF M25 Hong Kong | 2019/06/14 02:00 | Shintaro Imai v Xin Gao | 6-4,6-7,6-3 |
| ITF M25 Hong Kong | 2019/06/13 03:45 | Shintaro Imai v Hong Kit Wong | 6-3,3-6,6-1 |
| ITF M25 Hong Kong | 2019/06/12 02:55 | Shintaro Imai v N. Vijay Sundar Prashanth | 6-2,6-4 |