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| Erste Bank Open 500 | ||
| Surface: Hard | Date: Oct. 25 - Oct. 31 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Andy Murray | Loss | 4-6, 7-6 (8-6), 3-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Oct. 6 - Oct. 17 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Alexei Popyrin | Win | 6-1, 7-5 |
| Third Round | Frances Tiafoe | Win | 6-3, 6-2 |
| Fourth Round | Aslan Karatsev | Win | 6-1, 6-3 |
| Quarterfinals | Grigor Dimitrov | Loss | 6-3, 4-6, 6-7 (2-7) |
| San Diego Open | ||
| Surface: Hard | Date: Sep. 27 - Oct. 3 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Alex Bolt | Win | 7-6 (7-2), 6-1 |
| Second Round | Aslan Karatsev | Loss | 7-5, 4-6, 2-6 |
| Moselle Open | ||
| Surface: Hard | Date: Sep. 20 - Sep. 26 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Lucas Pouille | Win | 6-2, 6-3 |
| Quarterfinals | Andy Murray | Win | 7-6 (7-4), 6-3 |
| Semifinals | Peter Gojowczyk | Win | 6-4, 7-6 (7-4) |
| Final | Pablo Carreno Busta | Win | 7-6 (7-2), 6-3 |
| US Open | ||
| Surface: Hard | Date: Aug. 30 - Sep. 12 | Seed: 10 |
| Round | Opponent | W / L | Result |
| First Round | Egor Gerasimov | Win | 6-3, 6-4, 6-3 |
| Second Round | Andreas Seppi | Loss | 6-2, 4-6, 4-6, 6-7 (6-8) |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 15 - Aug. 22 | Seed: 9 |
| Round | Opponent | W / L | Result |
| First Round | Alejandro Davidovich Fokina | Win | 6-1, 6-7 (3-7), 6-1 |
| Second Round | Andy Murray | Win | 7-6 (7-4), 6-3 |
| Third Round | Pablo Carreno Busta | Loss | 6-7 (6-8), 6-7 (3-7) |
| Open de la Banque Nationale presentee par Rogers | ||
| Surface: Hard | Date: Aug. 9 - Aug. 15 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Kei Nishikori | Win | Retired |
| Third Round | Nikoloz Basilashvili | Win | 6-7 (7-9), 6-4, 6-4 |
| Quarterfinals | Daniil Medvedev | Loss | 6-2, 6-7 (6-8), 6-7 (5-7) |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 28 - Jul. 11 | Seed: 14 |
| Round | Opponent | W / L | Result |
| First Round | Lorenzo Musetti | Win | 6-4, 7-6 (7-5), 6-1 |
| Second Round | Marcos Giron | Win | 6-3, 6-2, 6-4 |
| Third Round | Alexander Bublik | Win | 6-3, 6-4, 6-2 |
| Fourth Round | Daniil Medvedev | Win | 2-6, 7-6 (7-2), 3-6, 6-3, 6-3 |
| Quarterfinals | Roger Federer | Win | 6-3, 7-6 (7-4), 6-0 |
| Semifinals | Matteo Berrettini | Loss | 3-6, 0-6, 7-6 (7-3), 4-6 |
| NOVENTI OPEN | ||
| Surface: Grass | Date: Jun. 14 - Jun. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Felix Auger-Aliassime | Loss | 3-6, 5-7 |
| MercedesCup | ||
| Surface: Grass | Date: Jun. 8 - Jun. 13 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Dominic Stephan Stricker | Loss | 6-7 (5-7), 6-7 (5-7) |
| Roland Garros | ||
| Surface: Red Clay | Date: May 30 - Jun. 13 | Seed: 19 |
| Round | Opponent | W / L | Result |
| First Round | Botic van de Zandschulp | Loss | 7-6 (7-5), 7-6 (7-4), 2-6, 2-6, 4-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 9 - May 16 | Seed: 15 |
| Round | Opponent | W / L | Result |
| First Round | Lorenzo Musetti | Loss | 4-6, 0-2 Retired |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 29 - May 9 | Seed: 12 |
| Round | Opponent | W / L | Result |
| First Round | John Millman | Loss | 7-5, 6-7 (7-9), 3-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 11 - Apr. 18 | Seed: 13 |
| Round | Opponent | W / L | Result |
| First Round | Thomas Fabbiano | Win | 6-3, 3-6, 6-3 |
| Second Round | Daniel Evans | Loss | 4-6, 1-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 23 - Apr. 4 | Seed: 26 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Denis Kudla | Win | 7-6 (7-5), 6-4 |
| Third Round | Denis Shapovalov | Win | 6-3, 7-6 (8-6) |
| Fourth Round | Milos Raonic | Win | 4-6, 6-3, 7-6 (7-4) |
| Quarterfinals | Stefanos Tsitsipas | Win | 2-6, 6-3, 6-4 |
| Semifinals | Andrey Rublev | Win | 6-3, 6-4 |
| Final | Jannik Sinner | Win | 7-6 (7-4), 6-4 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Mar. 14 - Mar. 20 | Seed: 13 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Richard Gasquet | Win | 6-3, 6-4 |
| Third Round | Denis Shapovalov | Loss | 4-6, 3-6 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Mar. 1 - Mar. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Adrian Mannarino | Win | 6-3, 7-6 (8-6) |
| Second Round | Stefanos Tsitsipas | Loss | 4-6, 6-4, 5-7 |
| Open Sud de France | ||
| Surface: Hard | Date: Feb. 22 - Feb. 28 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Alejandro Davidovich Fokina | Loss | 5-7, 2-6 |
| Australian Open | ||
| Surface: Hard | Date: Feb. 8 - Feb. 21 | Seed: 26 |
| Round | Opponent | W / L | Result |
| First Round | Mikael Ymer | Loss | 6-3, 3-6, 6-3, 5-7, 3-6 |
| Great Ocean Road Open | ||
| Surface: Hard | Date: Feb. 1 - Feb. 7 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Mikael Torpegaard | Win | 6-4, 6-3 |
| Third Round | Pablo Cuevas | Win | 7-5, 7-5 |
| Quarterfinals | Stefano Travaglia | Loss | 6-3, 3-6, 5-7 |
| Delray Beach Open by VITACOST.com | ||
| Surface: Hard | Date: Jan. 7 - Jan. 13 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Daniel Elahi Galan | Win | 6-2, 6-2 |
| Quarterfinals | Roberto Quiroz | Win | 6-4, 6-4 |
| Semifinals | Christian Harrison | Win | 7-6 (7-4), 6-4 |
| Final | Sebastian Korda | Win | 6-3, 6-3 |
