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| BNP Paribas Open | ||
| Surface: Hard | Date: Oct. 6 - Oct. 17 | Seed: 21 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Tennys Sandgren | Win | 6-4, 5-7, 6-0 |
| Third Round | Roberto Bautista Agut | Win | 6-4, 5-7, 6-3 |
| Fourth Round | Tommy Paul | Win | 6-4, 4-6, 6-2 |
| Quarterfinals | Diego Schwartzman | Win | 6-0, 6-2 |
| San Diego Open | ||
| Surface: Hard | Date: Sep. 27 - Oct. 3 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Dominik Koepfer | Win | 6-2, 7-5 |
| Second Round | Daniel Evans | Win | 7-6 (7-3), 6-3 |
| Quarterfinals | Denis Shapovalov | Win | 6-3, 6-1 |
| Semifinals | Andrey Rublev | Win | 3-6, 6-3, 6-4 |
| Final | Casper Ruud | Loss | 0-6, 2-6 |
| US Open | ||
| Surface: Hard | Date: Aug. 30 - Sep. 12 | Seed: 26 |
| Round | Opponent | W / L | Result |
| First Round | Carlos Alcaraz | Loss | 4-6, 4-6, 3-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 15 - Aug. 22 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | John Isner | Loss | 6-4, 6-7 (5-7), 4-6 |
| Open de la Banque Nationale presentee par Rogers | ||
| Surface: Hard | Date: Aug. 9 - Aug. 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Karen Khachanov | Loss | 4-6, 7-5, 4-6 |
| Citi Open | ||
| Surface: Hard | Date: Aug. 2 - Aug. 8 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Marcos Giron | Win | 6-4, 6-3 |
| Third Round | Kei Nishikori | Loss | 6-3, 3-6, 3-6 |
| Truist Atlanta Open | ||
| Surface: Hard | Date: Jul. 26 - Aug. 1 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Nick Kyrgios | Win | 6-1, 6-4 |
| Quarterfinals | Emil Ruusuvuori | Loss | 6-7 (1-7), 3-6 |
| Mifel Open | ||
| Surface: Hard | Date: Jul. 19 - Jul. 25 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Elias Ymer | Win | 7-6 (7-4), 6-3 |
| Quarterfinals | Ernesto Escobedo | Win | 6-1, 6-1 |
| Semifinals | Taylor Fritz | Win | 6-3, 6-1 |
| Final | Brandon Nakashima | Win | 6-2, 6-2 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 28 - Jul. 11 | Seed: 29 |
| Round | Opponent | W / L | Result |
| First Round | Lucas Pouille | Win | 6-7 (6-8), 7-5, 6-2, 7-5 |
| Second Round | Alex Bolt | Win | 6-3, 6-1, 6-2 |
| Third Round | Roger Federer | Loss | 4-6, 4-6, 7-5, 4-6 |
| cinch Championships | ||
| Surface: Grass | Date: Jun. 14 - Jun. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Albert Ramos-Vinolas | Win | 4-6, 6-3, 6-4 |
| Second Round | Aslan Karatsev | Win | 7-5, 6-2 |
| Quarterfinals | Jack Draper | Win | 6-3, 6-3 |
| Semifinals | Denis Shapovalov | Win | 7-5, 6-3 |
| Final | Matteo Berrettini | Loss | 4-6, 7-6 (7-5), 3-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 30 - Jun. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Bjorn Fratangelo | Win | 7-5, 7-6 (7-5), 6-2 |
| Second Round | Lloyd Harris | Win | 4-6, 6-3, 6-3, 6-2 |
| Third Round | Rafael Nadal | Loss | 3-6, 3-6, 3-6 |
| Open Parc Auvergne-Rhone-Alpes Lyon | ||
| Surface: Clay | Date: May 17 - May 23 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Corentin Moutet | Win | 7-5, 6-3 |
| Second Round | Dominic Thiem | Win | 6-3, 6-2 |
| Quarterfinals | Arthur Rinderknech | Win | 6-3, 3-6, 6-3 |
| Semifinals | Karen Khachanov | Win | 6-1, 6-1 |
| Final | Stefanos Tsitsipas | Loss | 3-6, 3-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 9 - May 16 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Roberto Carballes Baena | Win | 6-4, 6-4 |
| Second Round | Alejandro Davidovich Fokina | Loss | 2-6, 3-6 |
| Millennium Estoril Open | ||
| Surface: Red Clay | Date: Apr. 26 - May 2 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Joao Sousa | Win | 6-1, 6-3 |
| Second Round | Pedro Martinez | Win | 4-6, 7-6 (7-1), 7-5 |
| Quarterfinals | Cristian Garin | Win | 3-6, 7-5, 6-3 |
| Semifinals | Marin Cilic | Win | 7-6 (7-5), 7-5 |
| Final | Albert Ramos-Vinolas | Loss | 6-4, 3-6, 6-7 (3-7) |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 19 - Apr. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Salvatore Caruso | Win | 6-1, 6-2 |
| Second Round | Karen Khachanov | Win | 6-4, 3-6, 6-3 |
| Third Round | David Goffin | Win | 6-0, 3-5 Retired |
| Quarterfinals | Rafael Nadal | Loss | 1-6, 4-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 23 - Apr. 4 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Yoshihito Nishioka | Win | 6-1, 3-6, 7-5 |
| Second Round | Grigor Dimitrov | Win | 7-5, 7-5 |
| Third Round | Taylor Fritz | Loss | 4-6, 6-3, 1-6 |
| Abierto Mexicano Telcel presentado por HSBC | ||
| Surface: Hard | Date: Mar. 15 - Mar. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Stefan Kozlov | Win | 6-3, 6-3 |
| Second Round | Fabio Fognini | Win | 6-4, 6-3 |
| Quarterfinals | Dominik Koepfer | Loss | 5-7, 4-6 |
| Open 13 Provence | ||
| Surface: Hard | Date: Mar. 8 - Mar. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Constant Lestienne | Win | 6-4, 6-7 (4-7), 6-3 |
| Second Round | Pierre-Hugues Herbert | Loss | 3-6, 4-6 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Mar. 1 - Mar. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nikoloz Basilashvili | Win | 6-0, 6-3 |
| Second Round | Karen Khachanov | Loss | 2-6, 2-6 |
| Australian Open | ||
| Surface: Hard | Date: Feb. 8 - Feb. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Daniel Evans | Win | 6-4, 4-6, 6-4, 7-5 |
| Second Round | Roman Safiullin | Win | 3-6, 7-5, 6-3, 7-6(7-3) |
| Third Round | Rafael Nadal | Loss | 5-7, 2-6, 5-7 |
| Murray River Open | ||
| Surface: Hard | Date: Feb. 1 - Feb. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Tommy Paul | Loss | 6-4, 6-7 (2-7), 3-6 |
| Delray Beach Open by VITACOST.com | ||
| Surface: Hard | Date: Jan. 7 - Jan. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | JC Aragone | Win | 6-2, 6-1 |
| Second Round | Adrian Mannarino | Win | 6-2, 7-5 |
| Quarterfinals | Frances Tiafoe | Win | 6-0, 3-6, 6-4 |
| Semifinals | Sebastian Korda | Loss | 3-6, 5-7 |
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