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| VTB Kremlin Cup | ||
| Surface: Hard | Date: Oct. 18 - Oct. 24 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Adrian Mannarino | Loss | 7-5, 6-7 (4-7), 3-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Oct. 6 - Oct. 17 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Carlos Taberner | Win | 6-3, 6-4 |
| Third Round | Tommy Paul | Loss | 4-6, 6-3, 5-7 |
| San Diego Open | ||
| Surface: Hard | Date: Sep. 27 - Oct. 3 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Brandon Nakashima | Win | 6-2, 6-1 |
| Quarterfinals | Diego Schwartzman | Win | 6-1, 7-5 |
| Semifinals | Cameron Norrie | Loss | 6-3, 3-6, 4-6 |
| US Open | ||
| Surface: Hard | Date: Aug. 30 - Sep. 12 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Ivo Karlovic | Win | 6-3, 7-6 (7-3), 6-3 |
| Second Round | Pedro Martinez | Win | 7-6 (7-2), 6-7 (5-7), 6-1, 6-1 |
| Third Round | Frances Tiafoe | Loss | 6-4, 3-6, 6-7 (6-8), 6-4, 1-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 15 - Aug. 22 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Marin Cilic | Win | 5-7, 6-3, 6-1 |
| Third Round | Gael Monfils | Win | 7-6 (7-2), 7-6 (7-5) |
| Quarterfinals | Benoit Paire | Win | 6-2, 3-6, 6-3 |
| Semifinals | Daniil Medvedev | Win | 2-6, 6-3, 6-3 |
| Final | Alexander Zverev | Loss | 2-6, 3-6 |
| Open de la Banque Nationale presentee par Rogers | ||
| Surface: Hard | Date: Aug. 9 - Aug. 15 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Fabio Fognini | Win | 7-6 (7-4), 6-3 |
| Third Round | John Isner | Loss | 5-7, 6-7 (5-7) |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 28 - Jul. 11 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Federico Delbonis | Win | 4-6, 6-4, 6-1, 6-2 |
| Second Round | Lloyd Harris | Win | 6-1, 6-2, 7-5 |
| Third Round | Fabio Fognini | Win | 6-3, 5-7, 6-4, 6-2 |
| Fourth Round | Marton Fucsovics | Loss | 3-6, 6-4, 6-4, 0-6, 3-6 |
| NOVENTI OPEN | ||
| Surface: Grass | Date: Jun. 14 - Jun. 20 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Karen Khachanov | Win | 6-3, 7-6 (7-5) |
| Second Round | Jordan Thompson | Win | 6-4, 6-4 |
| Quarterfinals | Philipp Kohlschreiber | Win | 7-6 (7-4), 6-2 |
| Semifinals | Nikoloz Basilashvili | Win | 6-1, 3-6, 6-3 |
| Final | Ugo Humbert | Loss | 3-6, 6-7 (4-7) |
| Roland Garros | ||
| Surface: Red Clay | Date: May 30 - Jun. 13 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Jan-Lennard Struff | Loss | 3-6, 6-7 (6-8), 6-4, 6-3, 4-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 9 - May 16 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Jan-Lennard Struff | Win | 6-7 (7-9), 6-1, 6-4 |
| Third Round | Roberto Bautista Agut | Win | 6-4, 6-4 |
| Quarterfinals | Lorenzo Sonego | Loss | 6-3, 4-6, 3-6 |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 29 - May 9 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Tommy Paul | Win | 6-7 (5-7), 6-3, 6-4 |
| Third Round | John Isner | Loss | 6-7 (4-7), 6-3, 6-7 (4-7) |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 19 - Apr. 25 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Federico Gaio | Win | 6-4, 6-3 |
| Third Round | Albert Ramos-Vinolas | Win | 6-4, 6-7 (4-7), 6-4 |
| Quarterfinals | Jannik Sinner | Loss | 2-6, 6-7 (6-8) |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 11 - Apr. 18 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Salvatore Caruso | Win | 6-3, 6-2 |
| Third Round | Roberto Bautista Agut | Win | 7-6 (7-2), 5-7, 6-3 |
| Quarterfinals | Rafael Nadal | Win | 6-2, 4-6, 6-2 |
| Semifinals | Casper Ruud | Win | 6-3, 7-5 |
| Final | Stefanos Tsitsipas | Loss | 3-6, 3-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 23 - Apr. 4 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Tennys Sandgren | Win | 6-1, 6-2 |
| Third Round | Marton Fucsovics | Win | 6-2, 6-1 |
| Fourth Round | Marin Cilic | Win | 6-4, 6-4 |
| Quarterfinals | Sebastian Korda | Win | 7-5, 7-6 (9-7) |
| Semifinals | Hubert Hurkacz | Loss | 3-6, 4-6 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Mar. 14 - Mar. 20 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Emil Ruusuvuori | Win | 6-4, 6-4 |
| Third Round | Taylor Fritz | Win | 6-3, 6-1 |
| Quarterfinals | Marton Fucsovics | Win | 7-5, 6-2 |
| Semifinals | Aslan Karatsev | Loss | 2-6, 6-4, 4-6 |
| Qatar ExxonMobil Open | ||
| Surface: Hard | Date: Mar. 8 - Mar. 13 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Richard Gasquet | Win | Retired |
| Quarterfinals | Marton Fucsovics | Win | Retired |
| Semifinals | Roberto Bautista Agut | Loss | 3-6, 3-6 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Mar. 1 - Mar. 7 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Marcos Giron | Win | 7-6 (7-1), 6-3 |
| Second Round | Andy Murray | Win | 7-5, 6-2 |
| Quarterfinals | Jeremy Chardy | Win | 7-6 (7-2), 6-7 (2-7), 6-4 |
| Semifinals | Stefanos Tsitsipas | Win | 6-3, 7-6 (7-2) |
| Final | Marton Fucsovics | Win | 7-6 (7-4), 6-4 |
| Australian Open | ||
| Surface: Hard | Date: Feb. 8 - Feb. 21 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Yannick Hanfmann | Win | 6-3, 6-3, 6-4 |
| Second Round | Thiago Monteiro | Win | 6-4, 6-4, 7-6 (10-8) |
| Third Round | Feliciano Lopez | Win | 7-5, 6-2, 6-3 |
| Fourth Round | Casper Ruud | Win | 6-2, 7-6 (7-3), 0-0 Retired |
| Quarterfinals | Daniil Medvedev | Loss | 5-7, 3-6, 2-6 |
