stadio: Center Court Round: 24 Ground: Clay
| ATP Los Cabos | 2019/07/29 00:00 | Dominik Koepfer v Jacob Grills | 6-3,7-6 |
| ATP Los Cabos | 2019/07/28 01:25 | Jacob Grills v Lukas Lacko | 6-3,6-2 |
| Challenger Granby | 2019/07/22 17:30 | Cem Ilkel v Jacob Grills | 6-1,6-0 |
| Challenger Gatineau | 2019/07/16 18:10 | Yosuke Watanuki v Jacob Grills | 6-7,6-1,6-0 |
| 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 |
| Challenger Chengdu | 2019/08/01 03:00 | Di Wu v Hyeon Chung | 6-7,7-6,3-6 |
| Challenger Chengdu | 2019/07/30 06:55 | Di Wu v Chuhan Wang | 6-3,6-3 |
| Challenger Fergana | 2019/06/20 08:35 | Di Wu v Gleb Sakharov | 3-6,6-7 |
| Challenger Fergana | 2019/06/19 09:25 | Di Wu v Alexander Zhurbin | 6-0,7-6 |
| Challenger Shymkent 2 | 2019/06/11 04:00 | Di Wu v Andrey Golubev | 2-6,3-6 |
| Challenger Almaty | 2019/06/05 10:15 | Di Wu v Andrej Martin | 0-6,4-6 |
| Challenger Almaty | 2019/06/03 09:10 | Aleksandar Vukic v Di Wu | 4-6,6-2,3-6 |
| Challenger Gwangju | 2019/05/13 04:40 | Di Wu v Roy Smith | 2-6,4-6 |