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| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 14 - Aug. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Karen Khachanov | Win | 6-3, 6-4 |
| Second Round | Frances Tiafoe | Win | 4-6, 6-1, 6-4 |
| Third Round | John Isner | Loss | 6-7 (3-7), 6-1, 6-7 (4-7) |
| Citi Open | ||
| Surface: Hard | Date: Aug. 1 - Aug. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ilya Ivashka | Win | 6-4, 7-6 (7-5) |
| Second Round | Sebastian Baez | Win | 6-1, 6-4 |
| Third Round | Grigor Dimitrov | Win | 4-6, 6-1, 6-2 |
| Quarterfinals | Mikael Ymer | Loss | 2-6, 7-5, 3-6 |
| Atlanta Open | ||
| Surface: Hard | Date: Jul. 25 - Jul. 31 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Taro Daniel | Loss | 6-1, 1-6, 3-6 |
| Rothesay International Eastbourne | ||
| Surface: Grass | Date: Jun. 19 - Jun. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | John Millman | Loss | 3-6, 6-7 (5-7) |
| Terra Wortmann Open | ||
| Surface: Grass | Date: Jun. 13 - Jun. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Cristian Garin | Win | 6-2, 6-3 |
| Second Round | Pablo Carreno Busta | Loss | 4-6, 6-0, 3-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 22 - Jun. 5 | Seed: 27 |
| Round | Opponent | W / L | Result |
| First Round | John Millman | Win | 6-1, 7-5, 7-6 (8-6) |
| Second Round | Richard Gasquet | Win | 7-6 (7-5), 6-3, 6-3 |
| Third Round | Carlos Alcaraz | Loss | 4-6, 4-6, 2-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 8 - May 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Botic van de Zandschulp | Loss | 4-6, 1-6 |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 28 - May 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Reilly Opelka | Win | 6-3, 7-5 |
| Second Round | Lorenzo Musetti | Loss | 4-6, 3-6 |
| Millennium Estoril Open | ||
| Surface: Red Clay | Date: Apr. 25 - May 1 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Pierre-Hugues Herbert | Win | 6-2, 6-4 |
| Second Round | Benjamin Bonzi | Win | 6-3, 6-3 |
| Quarterfinals | Felix Auger-Aliassime | Win | 6-2, 6-2 |
| Semifinals | Frances Tiafoe | Loss | 6-4, 6-7 (2-7), 4-6 |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 18 - Apr. 24 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Carlos Taberner | Loss | 3-6, 0-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 10 - Apr. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Botic van de Zandschulp | Win | 7-5, 6-4 |
| Second Round | Carlos Alcaraz | Win | 7-6 (7-2), 6-7 (5-7), 6-3 |
| Third Round | Taylor Fritz | Loss | 6-7 (4-7), 5-7 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 3 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alejandro Davidovich Fokina | Win | 6-1, 6-1 |
| Second Round | Albert Ramos-Vinolas | Win | 4-6, 7-6 (8-6), 6-3 |
| Third Round | Miomir Kecmanovic | Loss | 6-7 (4-7), 3-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 9 - Mar. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Thanasi Kokkinakis | Win | 6-3, 6-4 |
| Second Round | Rafael Nadal | Loss | 2-6, 6-1, 6-7 (3-7) |
| Abierto Mexicano Telcel presentado por HSBC | ||
| Surface: Hard | Date: Feb. 21 - Feb. 26 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Dusan Lajovic | Loss | 4-6, 6-4, 5-7 |
| Delray Beach Open by VITACOST.com | ||
| Surface: Hard | Date: Feb. 14 - Feb. 20 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Thanasi Kokkinakis | Win | 6-4, 6-1 |
| Second Round | Andreas Seppi | Win | 7-5, 6-3 |
| Quarterfinals | Cameron Norrie | Loss | 2-6, 6-1, 6-7 (4-7) |
| Australian Open | ||
| Surface: Hard | Date: Jan. 17 - Jan. 30 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Cameron Norrie | Win | 6-3, 6-0, 6-4 |
| Second Round | Corentin Moutet | Win | 3-6, 6-4, 6-7 (2-7), 7-5, 7-6 (10-6) |
| Third Round | Pablo Carreno Busta | Loss | 4-6, 5-7, 7-6 (8-6), 3-6 |
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