Stadium: Court 2 Round: 25 Ground: Hardcourt outdoor
| Challenger Pune | 2019/11/11 08:50 | Timur Khabibulin v Anirudh Chandrasekar | 6-4,4-6,3-6 |
| ITF M15 Maputo | 2019/11/06 07:00 | Anirudh Chandrasekar v Eric Vanshelboim | 1-6,2-6 |
| ITF M15 Nanchang | 2019/10/02 08:30 | Anirudh Chandrasekar v Daisuke Sumizawa | 6-3,2-6,1-6 |
| ITF M15 Nanchang | 2019/09/26 02:00 | Anirudh Chandrasekar v Takashi Saito | 7-5,0-6,0-6 |
| ITF M15 Nanchang | 2019/09/25 04:05 | Xian Yao Zhou v Anirudh Chandrasekar | 4-6,1-6 |
| ITF M15 Nanchang | 2019/09/23 07:15 | Anirudh Chandrasekar v Tomohiro Masabayashi | 6-1,7-6 |
| ITF M15 Nanchang | 2019/09/23 02:00 | Anirudh Chandrasekar v Bingyu Yu | 6-1,6-4 |
| ITF M15 Nanchang | 2019/09/22 02:00 | Anirudh Chandrasekar v Cheng Han | 7-6,6-3 |
| ITF M25 Monastir | 2019/10/26 09:00 | Roberto Ortega-Olmedo v Petros Chrysochos | 3-6,1-6 |
| ITF M25 Monastir | 2019/10/25 09:00 | Roberto Ortega-Olmedo v Filip Bergevi | 6-3,6-3 |
| ITF M25 Monastir | 2019/10/24 10:50 | Roberto Ortega-Olmedo v Maksim Tikhomirov | 6-2,6-4 |
| ITF M25 Monastir | 2019/10/22 11:40 | Roberto Ortega-Olmedo v Anis Ghorbel | 6-1,6-1 |
| Challenger Ismaning | 2019/10/14 09:20 | Lucas Miedler v Roberto Ortega-Olmedo | 7-6,6-4 |
| ITF M25 Tavira | 2019/10/04 09:00 | Roberto Ortega-Olmedo v Eduardo Struvay | 4-6,2-6 |
| ITF M25 Tavira | 2019/10/03 09:00 | Roberto Ortega-Olmedo v Tomas Luis | 6-4,6-2 |
| ITF M25 Tavira | 2019/10/02 10:00 | Roberto Ortega-Olmedo v Francisco Cabral | 6-4,3-6,6-4 |