01/By surface
each with its own count, at equal weight
Hard
0-1
G. leads 1-0 in 1 meeting on hard
Clay
0-1
G. leads 1-0 in 1 meeting on clay
Grass
1-1
Level 1-1 in 2 meetings on grass
02/Every meeting
4 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, D. first |
|---|---|---|---|---|---|---|
| Jun 9, 2022 | Rosmalen Grass Court ChampionshipsATP250 | grass | 2nd round | Medvedev D. | 7-5, 6-4 | 2 v 134 |
| Feb 21, 2020 | Open 13ATP250 | hard | quarterfinal | Simon G. | 6-4, 6-0 | 5 v 58 |
| Jun 22, 2019 | Queen's Club ChampionshipsATP500 | grass | semifinal | Simon G. | 6-7, 6-4, 6-3 | 13 v 38 |
| May 22, 2017 | Lyon OpenATP250 | clay | 1st round | Simon G. | 7-5, 6-7, 6-2 | 65 v 32 |
A record, never a share of meetings. Main-draw singles since 2013; a meeting ended by retirement is counted with the sets that were played and marked; a walkover is listed and counted in neither column. Medvedev D. and Simon G. each carry the table against every opponent faced.