[88] Prajnesh Gunneswaran 4-6,1-6,2-6 Daniil Medvedev [5] 2019-08-26 17:05
Stadium: Louis Armstrong Stadium Round: 23 Ground: Hardcourt outdoor
Home History
| 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 |
| ATP Antalya | 2019/06/25 12:30 | Lorenzo Sonego v Prajnesh Gunneswaran | 6-7,6-0,7-5 |
Away History
| ATP Cincinnati | 2019/08/18 20:00 | Daniil Medvedev v David Goffin | 7-6,6-4 |
| ATP Cincinnati | 2019/08/17 22:00 | Novak Djokovic v Daniil Medvedev | 6-3,3-6,3-6 |
| ATP Cincinnati | 2019/08/16 23:00 | Andrey Rublev v Daniil Medvedev | 2-6,3-6 |
| ATP Cincinnati | 2019/08/15 17:25 | Daniil Medvedev v Jan-Lennard Struff | 6-2,6-1 |
| ATP Cincinnati | 2019/08/14 16:55 | Daniil Medvedev v Benoit Paire | 7-6,6-1 |
| ATP Cincinnati | 2019/08/13 19:40 | Daniil Medvedev v Kyle Edmund | 6-2,7-5 |
| ATP Montreal | 2019/08/11 20:00 | Rafael Nadal v Daniil Medvedev | 6-3,6-0 |
| ATP Montreal | 2019/08/10 21:50 | Karen Khachanov v Daniil Medvedev | 1-6,6-7 |