Stadium: Center Round: 26 Ground: Hardcourt outdoor
| Challenger Shanghai | 2019/09/10 08:15 | Marc Polmans v Wu, Di | 3-6,3-6 |
| Jinan, China | 2019/09/05 03:00 | Wu, Di v Soeda, Go | 2-6,1-6 |
| Jinan, China | 2019/09/03 06:30 | Hiroki Moriya v Wu, Di | 3-6,5-7 |
| Jinan, China | 2019/09/02 04:30 | Wu, Di v Collin Altamirano | 6-4,6-4 |
| Baotou, Chine | 2019/08/27 07:05 | Tung-Lin Wu v Wu, Di | 3-6,6-1,7-5 |
| Baotou, Chine | 2019/08/26 02:00 | Grills, Jacob v Wu, Di | 6-7,4-6 |
| Chengdu, China | 2019/08/01 03:00 | Wu, Di v Chung, Hyeon | 6-7,7-6,3-6 |
| Chengdu, China | 2019/07/30 06:55 | Wu, Di v Wang, Chuhan | 6-3,6-3 |
| Challenger Shanghai | 2019/09/10 07:25 | He, Yecong v Ortega-Olmedo, Roberto | 2-6,3-6 |
| Jinan, China | 2019/09/04 02:00 | Tung-Lin Wu v Ortega-Olmedo, Roberto | 5-7,6-2,7-5 |
| Baotou, Chine | 2019/08/29 02:00 | Frederico Ferreira Silva v Ortega-Olmedo, Roberto | 6-1,6-1 |
| Baotou, Chine | 2019/08/28 02:00 | Hamou, Maxime v Ortega-Olmedo, Roberto | 6-7,6-7 |
| Challenger Meerbusch | 2019/08/16 12:30 | Ortega-Olmedo, Roberto v Krstin, Pedja | 0-6,2-6 |
| Challenger Meerbusch | 2019/08/15 10:30 | Ortega-Olmedo, Roberto v Raul Brancaccio | 6-4,6-7,6-4 |
| Challenger Meerbusch | 2019/08/14 09:20 | Ortega-Olmedo, Roberto v Pavlasek, Adam | 6-3,6-4 |
| Pozoblanco, Singles Qualifying M-ITF-ESP-24A | 2019/08/08 18:00 | Ortega-Olmedo, Roberto v Lescure, Mick | 6-4,3-6,4-6 |