Stadium: Holcim Stadium 3 Round: 24 Ground: Hardcourt outdoor
| ATP Madrid | 2018/05/08 17:00 | Daniil Medvedev v Kyle Edmund | 4-6,0-6 |
| ATP Winston-Salem | 2017/08/22 19:00 | Daniil Medvedev v Kyle Edmund | 6-2,2-6,6-7 |
| ATP Stuttgart | 2019/06/12 16:35 | Lucas Pouille v Daniil Medvedev | 7-6,4-6,6-2 |
| French Open | 2019/05/27 09:00 | Pierre-Hugues Herbert v Daniil Medvedev | 4-6,4-6,6-3,6-2,7-5 |
| ATP Rome | 2019/05/14 10:35 | Daniil Medvedev v Nick Kyrgios | 3-6,6-3,3-6 |
| ATP Madrid | 2019/05/07 10:00 | Guido Pella v Daniil Medvedev | 6-2,1-6,6-3 |
| ATP Barcelona | 2019/04/28 14:00 | Dominic Thiem v Daniil Medvedev | 6-4,6-0 |
| ATP Barcelona | 2019/04/27 11:30 | Kei Nishikori v Daniil Medvedev | 4-6,6-3,5-7 |
| ATP Barcelona | 2019/04/26 10:30 | Daniil Medvedev v Nicolas Jarry | 6-3,6-4 |
| ATP Barcelona | 2019/04/25 09:00 | Daniil Medvedev v Mackenzie McDonald | 6-3,6-2 |
| French Open | 2019/05/27 15:15 | Jeremy Chardy v Kyle Edmund | 6-7,7-5,4-6,6-4,5-7 |
| ATP Rome | 2019/05/13 09:00 | Fernando Verdasco v Kyle Edmund | 4-6,6-4,6-2 |
| ATP Madrid | 2019/05/07 12:00 | Fabio Fognini v Kyle Edmund | 6-4,6-3 |
| ATP Munich | 2019/04/30 14:10 | Kyle Edmund v Denis Kudla | 4-6,3-6 |
| ATP Monte Carlo | 2019/04/15 15:20 | Diego Schwartzman v Kyle Edmund | 4-6,6-3,6-1 |
| ATP Marrakech | 2019/04/10 15:45 | Kyle Edmund v Jo-Wilfried Tsonga | 6-7,3-6 |
| ATP Marrakech | 2019/04/08 14:10 | Kyle Edmund v Ugo Humbert | 6-3,6-2 |
| ATP Miami | 2019/03/26 16:00 | Kyle Edmund v John Isner | 6-7,6-7 |