Stadium: Center Round: 25 Ground: Hardcourt outdoor
| Challenger Shanghai | 2019/09/09 02:00 | Toshihide Matsui v Chuhan Wang | 5-7,6-7 |
| Challenger Yokkaichi | 2019/08/07 02:00 | Toshihide Matsui v Makoto Ochi | 7-6,7-6 |
| Challenger Yokkaichi | 2019/08/06 01:00 | Toshihide Matsui v John Paul Fruttero | 6-3,7-6 |
| Challenger Chengdu | 2019/07/30 03:35 | Manish Sureshkumar v Toshihide Matsui | 6-7,4-6 |
| Challenger Chengdu | 2019/07/29 04:30 | Toshihide Matsui v Yang Xuan Li | 6-2,6-3 |
| Challenger Winnipeg | 2019/07/10 20:05 | Toshihide Matsui v Enzo Couacaud | 3-6,2-6 |
| Challenger Winnipeg | 2019/07/09 15:00 | Alexander Lebedev v Toshihide Matsui | 6-7,4-6 |
| Challenger Winnipeg | 2019/07/08 16:00 | Toshihide Matsui v Kevin Kylar | 6-2,3-6,6-2 |
| US Open | 2019/08/22 15:00 | Jiri Vesely v Jason Jung | 6-4,5-7,7-5 |
| US Open | 2019/08/20 16:15 | Donald Young v Jason Jung | 3-6,7-6,5-7 |
| Challenger Vancouver | 2019/08/18 21:15 | Ricardas Berankis v Jason Jung | 6-3,5-7,6-4 |
| Challenger Vancouver | 2019/08/17 22:00 | Maxime Janvier v Jason Jung | 5-7,6-7 |
| Challenger Vancouver | 2019/08/16 23:35 | Jason Jung v Marc Polmans | 5-7,6-4,6-4 |
| Challenger Vancouver | 2019/08/15 19:30 | Evgeny Donskoy v Jason Jung | 6-4,3-6,4-6 |
| Challenger Vancouver | 2019/08/13 17:00 | Ruben Bemelmans v Jason Jung | 4-6,2-6 |
| ATP Los Cabos | 2019/07/30 03:10 | Ernests Gulbis v Jason Jung | 6-4,7-6 |