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| VTB Kremlin Cup | ||
| Surface: Hard | Date: Oct. 14 - Oct. 20 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Alexander Bublik | Win | 6-1, 3-6, 6-4 |
| Second Round | Egor Gerasimov | Win | 7-6 (7-3), 6-7 (6-8), 6-2 |
| Quarterfinals | Nikola Milojevic |
| Rolex Shanghai Masters | ||
| Surface: Hard | Date: Oct. 6 - Oct. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Borna Coric | Win | 6-4, 7-6 (7-4) |
| Second Round | John Millman | Win | 6-2, 6-0 |
| Third Round | Alexander Zverev | Loss | 0-6, 6-7 (4-7) |
| China Open | ||
| Surface: Hard | Date: Sep. 28 - Oct. 6 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Grigor Dimitrov | Win | 6-2, 7-5 |
| Second Round | Fabio Fognini | Loss | 3-6, 4-6 |
| St. Petersburg Open | ||
| Surface: Hard | Date: Sep. 16 - Sep. 22 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Ilya Ivashka | Win | 4-6, 6-0, 6-4 |
| Second Round | Ricardas Berankis | Win | 6-4, 6-7 (5-7), 6-1 |
| Quarterfinals | Daniil Medvedev | Loss | 4-6, 5-7 |
| US Open | ||
| Surface: Hard | Date: Aug. 26 - Sep. 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Stefanos Tsitsipas | Win | 6-4, 6-7 (5-7), 7-6 (9-7), 7-5 |
| Second Round | Gilles Simon | Win | 6-2 Retired |
| Third Round | Nick Kyrgios | Win | 7-6 (7-5), 7-6 (7-5), 6-3 |
| Fourth Round | Matteo Berrettini | Loss | 1-6, 4-6, 6-7 (6-8) |
| Winston-Salem Open | ||
| Surface: Hard | Date: Aug. 18 - Aug. 24 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Thomas Fabbiano | Win | 6-4, 6-2 |
| Second Round | Albert Ramos-Vinolas | Win | 6-7 (5-7), 6-3, 6-1 |
| Third Round | Sam Querrey | Win | 7-6 (7-4), 7-6 (12-10) |
| Quarterfinals | Denis Shapovalov | Loss | 3-6, 6-7 (4-7) |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 11 - Aug. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nikoloz Basilashvili | Win | 6-7 (4-7), 6-4, 6-2 |
| Second Round | Stan Wawrinka | Win | 6-4, 6-4 |
| Third Round | Roger Federer | Win | 6-3, 6-4 |
| Quarterfinals | Daniil Medvedev | Loss | 2-6, 3-6 |
| Citi Open | ||
| Surface: Hard | Date: Jul. 29 - Aug. 4 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Peter Gojowczyk | Loss | 6-7 (6-8), 6-4, 6-7 (2-7) |
| Hamburg Open | ||
| Surface: Red Clay | Date: Jul. 22 - Jul. 28 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Cristian Garin | Win | 6-4, 7-6 (7-5) |
| Second Round | Casper Ruud | Win | 3-6, 7-5, 6-3 |
| Quarterfinals | Dominic Thiem | Win | 7-6 (7-3), 7-6 (7-5) |
| Semifinals | Pablo Carreno Busta | Win | 4-6, 7-5, 6-1 |
| Final | Nikoloz Basilashvili | Loss | 5-7, 6-4, 3-6 |
| Plava Laguna Croatia Open Umag | ||
| Surface: Clay | Date: Jul. 15 - Jul. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Robin Haase | Win | 6-3, 6-2 |
| Second Round | Dusan Lajovic | Loss | 4-6, 3-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 1 - Jul. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Cristian Garin | Win | 4-6, 6-4, 7-5, 6-4 |
| Second Round | Sam Querrey | Loss | 3-6, 2-6, 3-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 14 - Apr. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Fabio Fognini | Loss | 6-4, 5-7, 4-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 19 - Mar. 31 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Taro Daniel | Win | 3-6, 6-3, 6-4 |
| Second Round | Marin Cilic | Win | 6-4, 6-4 |
| Third Round | Denis Shapovalov | Loss | 3-6, 6-7 (5-7) |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 6 - Mar. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Robin Haase | Win | 6-3, 3-6, 6-3 |
| Third Round | Karen Khachanov | Loss | 5-7, 3-6 |
| Open 13 Provence | ||
| Surface: Hard | Date: Feb. 18 - Feb. 24 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jo-Wilfried Tsonga | Win | 2-6, 6-4, 6-2 |
| Second Round | Matteo Berrettini | Win | 6-3, 7-6 (7-2) |
| Quarterfinals | Mikhail Kukushkin | Loss | 4-6, 1-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 14 - Jan. 27 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Mackenzie McDonald | Loss | 4-6, 4-6, 6-2, 4-6 |
| Sydney International | ||
| Surface: Hard | Date: Jan. 6 - Jan. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Lucas Pouille | Win | 6-2, 6-3 |
| Second Round | Yoshihito Nishioka | Loss | 3-6, 1-6 |
| Qatar ExxonMobil Open | ||
| Surface: Hard | Date: Dec. 31 - Jan. 5 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Andreas Seppi | Win | 7-5, 6-1 |
| Second Round | Nikoloz Basilashvili | Loss | 3-6, 4-6 |
