| 17‑Feb‑2020 | Marseille | Hard | QF | 5 | 58 | Gilles Simon [FRA] d. (1)Medvedev | 6-4 6-0 | (ch) | 0.35 | 0.0% | 0.0% | 56.6% | 50.0% | 39.1% | 1/6 | 1:07 |
| 5‑Aug‑2019 | Canada Masters | Hard | F | 9 | 2 | (1)Rafael Nadal [ESP] d. (8)Medvedev | 6-3 6-0 | (ch) | 0.49 | 10.2% | 10.2% | 63.3% | 61.3% | 33.3% | 4/8 | 1:10 |
| 22‑Apr‑2019 | Barcelona | Clay | F | 14 | 5 | (3)Dominic Thiem [AUT] d. (7)Medvedev | 6-4 6-0 | (ch) | 0.54 | 0.0% | 6.1% | 51.0% | 36.0% | 45.8% | 3/8 | 1:13 |
| 7‑May‑2018 | Madrid Masters | Clay | R64 | 51 | 22 | Kyle Edmund [GBR] d. Medvedev | 6-4 6-0 | | 0.73 | 5.8% | 9.6% | 57.7% | 56.7% | 40.9% | 3/7 | 1:17 |
| 5‑Feb‑2018 | Montpellier | Hard | R32 | 56 | 33 | (5)Richard Gasquet [FRA] d. Medvedev | 6-0 6-3 | | 0.46 | 1.9% | 5.8% | 57.7% | 53.3% | 40.9% | 8/13 | 0:56 |
| 24‑Apr‑2017 | Budapest | Clay | R32 | 63 | 184 | (Q)Laslo Djere [SRB] d. Medvedev | 6-0 5-5 RET | | 0.65 | 3.1% | 3.1% | 42.2% | 59.3% | 43.2% | 7/11 | 1:24 |
| 8‑Jun‑2015 | Moscow CH | Clay | R16 | 408 | 134 | (7)Daniel Munoz De La Nava [ESP] d. (WC)Medvedev | 6-0 7-6(8) | | 0.60 | 5.2% | 3.9% | 46.8% | 66.7% | 43.9% | 8/12 | |
| 14‑Oct‑2013 | Moscow | Hard | Q1 | | 307 | Victor Baluda [RUS] d. (WC)Medvedev | 6-4 6-0 | | 0.72 | 12.8% | 14.9% | 51.1% | 75.0% | 21.7% | 6/11 | 0:59 |
