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| Next Gen ATP Finals | ||
| Surface: Hard | Date: Nov. 5 - Nov. 9 | Seed: 1 |
| Round | Opponent | W / L | Result |
| Round Robin | Alejandro Davidovich Fokina | Win | 4-2, 3-4 (5-7), 4-1, 4-1 4-1, 4-3 (7-4), 1-4, 4-0 4-1, 4-0, 4-2 |
| Round Robin | Miomir Kecmanovic | Win | 4-2, 3-4 (5-7), 4-1, 4-1 4-1, 4-3 (7-4), 1-4, 4-0 4-1, 4-0, 4-2 |
| Round Robin | Casper Ruud | Win | 4-2, 3-4 (5-7), 4-1, 4-1 4-1, 4-3 (7-4), 1-4, 4-0 4-1, 4-0, 4-2 |
| Semifinals | Frances Tiafoe | Win | 4-2, 4-1, 0-4, 4-2 |
| Final | Jannik Sinner | Loss | 2-4, 1-4, 2-4 |
| Rolex Paris Masters | ||
| Surface: Hard | Date: Oct. 28 - Nov. 3 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Laslo Djere | Win | 6-1, 6-4 |
| Second Round | Roberto Bautista Agut | Win | 7-6 (7-2), 7-6 (7-1) |
| Third Round | Stefanos Tsitsipas | Loss | 3-6, 4-6 |
| Swiss Indoors Basel | ||
| Surface: Hard | Date: Oct. 21 - Oct. 27 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Hugo Dellien | Win | 6-1, 7-5 |
| Second Round | Taylor Fritz | Win | 6-3, 6-3 |
| Quarterfinals | Jan-Lennard Struff | Win | 6-4, 7-6 (7-4) |
| Semifinals | Reilly Opelka | Win | 7-6 (7-2), 6-7 (4-7), 7-6 (7-3) |
| Final | Roger Federer | Loss | 2-6, 2-6 |
| Rolex Shanghai Masters | ||
| Surface: Hard | Date: Oct. 6 - Oct. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | John Isner | Loss | 6-7 (1-7), 4-6 |
| Rakuten Japan Open Tennis Championships | ||
| Surface: Hard | Date: Sep. 30 - Oct. 6 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Lloyd Harris | Loss | 3-6, 7-6 (8-6), 6-7 (8-10) |
| Zhuhai Open | ||
| Surface: Hard | Date: Sep. 23 - Sep. 29 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | John Millman | Win | 6-1, 6-3 |
| Second Round | Andy Murray | Win | 4-6, 6-2, 6-4 |
| Quarterfinals | Borna Coric | Win | 6-2, 4-6, 6-4 |
| Semifinals | Roberto Bautista Agut | Win | 6-2, 6-2 |
| Final | Adrian Mannarino | Win | 7-6 (7-4), 6-4 |
| US Open | ||
| Surface: Hard | Date: Aug. 26 - Sep. 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Pierre-Hugues Herbert | Win | 6-4, 6-2, 6-7 (6-8), 7-5 |
| Second Round | Cristian Garin | Win | 6-3, 7-5, 6-3 |
| Third Round | Kei Nishikori | Win | 6-2, 6-4, 2-6, 6-3 |
| Fourth Round | Grigor Dimitrov | Loss | 5-7, 3-6, 4-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 11 - Aug. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marco Cecchinato | Win | 6-7 (5-7), 6-1, 6-2 |
| Second Round | Reilly Opelka | Win | 7-6 (7-3), 6-4 |
| Third Round | Yoshihito Nishioka | Loss | 5-7, 4-6 |
| Coupe Rogers presentee par Banque Nationale | ||
| Surface: Hard | Date: Aug. 5 - Aug. 11 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Daniel Evans | Loss | 4-6, 6-7 (6-8) |
| Citi Open | ||
| Surface: Hard | Date: Jul. 29 - Aug. 4 | Seed: 12 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Peter Gojowczyk | Loss | 3-6, 6-7 (6-8) |
| BB&T Atlanta Open | ||
| Surface: Hard | Date: Jul. 22 - Jul. 28 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Bradley Klahn | Win | 6-4, 6-4 |
| Quarterfinals | Bernard Tomic | Win | 6-2, 3-0 Retired |
| Semifinals | Reilly Opelka | Win | 7-6 (7-4), 6-7 (5-7), 6-3 |
| Final | Taylor Fritz | Win | 6-3, 7-6 (7-2) |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 1 - Jul. 14 | Seed: 25 |
| Round | Opponent | W / L | Result |
| First Round | Marco Cecchinato | Win | 6-0, 6-4, 7-6 (7-5) |
| Second Round | Steve Johnson | Loss | 6-3, 6-7 (4-7), 3-6, 6-3, 3-6 |
| Fever-Tree Championships | ||
| Surface: Grass | Date: Jun. 17 - Jun. 23 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Aljaz Bedene | Loss | 6-3, 4-6, 4-6 |
| Libema Open | ||
| Surface: Grass | Date: Jun. 10 - Jun. 16 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Andreas Seppi | Win | 7-5, 6-3 |
| Quarterfinals | Jordan Thompson | Loss | 6-4, 2-6, 3-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 26 - Jun. 9 | Seed: 21 |
| Round | Opponent | W / L | Result |
| First Round | Bradley Klahn | Win | 6-1, 6-4, 6-4 |
| Second Round | Pablo Carreno Busta | Loss | 3-6, 1-6, 1-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 12 - May 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marco Cecchinato | Loss | 6-4, 3-6, 1-6 |
| Mutua Madrid Open | ||
| Surface: Hard | Date: May 4 - May 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Hubert Hurkacz | Loss | 3-6, 4-6 |
| Millennium Estoril Open | ||
| Surface: Red Clay | Date: Apr. 29 - May 5 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Joao Domingues | Loss | 2-6, 6-2, 2-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 6 - Mar. 17 | Seed: 23 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Marcos Giron | Loss | 6-1, 4-6, 2-6 |
| Abierto Mexicano TELCEL presentado por HSBC | ||
| Surface: Hard | Date: Feb. 25 - Mar. 3 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Nicolas Jarry | Win | 7-6 (7-5), 7-6 (7-2) |
| Second Round | Feliciano Lopez | Win | Retired |
| Quarterfinals | Alexander Zverev | Loss | 4-6, 4-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 14 - Jan. 27 | Seed: 27 |
| Round | Opponent | W / L | Result |
| First Round | Pedro Sousa | Win | 6-4, 7-5, 6-4 |
| Second Round | Henri Laaksonen | Win | 6-4, 6-2, 6-7 (7-9), 4-6, 6-3 |
| Third Round | Rafael Nadal | Loss | 1-6, 2-6, 4-6 |
| Sydney International | ||
| Surface: Hard | Date: Jan. 6 - Jan. 12 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Dusan Lajovic | Win | 6-4, 6-3 |
| Second Round | Reilly Opelka | Win | 6-4, 7-6 (7-5) |
| Quarterfinals | Jordan Thompson | Win | 7-6 (7-4), 6-3 |
| Semifinals | Gilles Simon | Win | 6-3, 6-2 |
| Final | Andreas Seppi | Win | 7-5, 7-6 (7-5) |
| Brisbane International presented by Suncorp | ||
| Surface: Hard | Date: Dec. 31 - Jan. 6 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Alexei Popyrin | Win | 6-2, 6-2 |
| Second Round | Jordan Thompson | Win | 6-4, 6-2 |
| Quarterfinals | Jo-Wilfried Tsonga | Loss | 4-6, 6-7 (2-7) |
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