Stadium: Court 5 Round: 23 Ground: Hardcourt outdoor
| US Open | 2019/08/20 19:40 | Sumit Nagal v Tatsuma Ito | 7-6,6-2 |
| Challenger Yokkaichi | 2019/08/10 04:25 | Tatsuma Ito v James Duckworth | 3-6,4-6 |
| Challenger Yokkaichi | 2019/08/09 04:30 | Saketh Myneni v Tatsuma Ito | 6-7,1-6 |
| Challenger Yokkaichi | 2019/08/08 08:10 | Shinji Hazawa v Tatsuma Ito | 0-6,3-6 |
| Challenger Yokkaichi | 2019/08/07 08:15 | Kento Takeuchi v Tatsuma Ito | 6-7,1-6 |
| Challenger Chengdu | 2019/08/03 05:30 | Tatsuma Ito v Hyeon Chung | 2-6,6-7 |
| Challenger Chengdu | 2019/08/02 09:15 | Shuichi Sekiguchi v Tatsuma Ito | 2-6,1-6 |
| Challenger Chengdu | 2019/08/01 06:15 | Matthew Romios v Tatsuma Ito | 2-6,1-6 |
| US Open | 2019/08/26 17:05 | Prajnesh Gunneswaran v Daniil Medvedev | 4-6,1-6,2-6 |
| ATP Winston-Salem | 2019/08/20 18:25 | Benoit Paire v Prajnesh Gunneswaran | 6-3,7-5 |
| ATP Winston-Salem | 2019/08/18 21:15 | Prajnesh Gunneswaran v Cedrik-Marcel Stebe | 6-3,6-4 |
| ATP Los Cabos | 2019/08/01 01:50 | Prajnesh Gunneswaran v Taylor Fritz | 6-4,3-6,2-6 |
| ATP Los Cabos | 2019/07/30 00:00 | Prajnesh Gunneswaran v John Millman | 6-4,1-6,6-2 |
| ATP Atlanta | 2019/07/23 16:30 | Soonwoo Kwon v Prajnesh Gunneswaran | 6-7,7-5,6-0 |
| ATP Newport | 2019/07/15 17:25 | Marcel Granollers v Prajnesh Gunneswaran | 6-2,6-2 |
| Wimbledon | 2019/07/01 15:05 | Prajnesh Gunneswaran v Milos Raonic | 6-7,4-6,2-6 |