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| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 14 - Aug. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ben Shelton | Loss | 6-7 (5-7), 6-3, 5-7 |
| Generali Open | ||
| Surface: Clay | Date: Jul. 25 - Jul. 30 | Seed: 9 |
| Round | Opponent | W / L | Result |
| First Round | Pablo Andujar | Loss | 4-6, 6-3, 6-7 (4-7) |
| EFG Suisse Open Gstaad | ||
| Surface: Clay | Date: Jul. 18 - Jul. 24 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Juan Pablo Varillas | Loss | 6-7 (5-7), 2-6 |
| Nordea Open | ||
| Surface: Clay | Date: Jul. 11 - Jul. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Aslan Karatsev | Loss | 0-6, 6-2, 4-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 27 - Jul. 10 | Seed: 27 |
| Round | Opponent | W / L | Result |
| First Round | Denis Kudla | Win | 6-7 (6-8), 6-3, 7-5, 4-6, 6-2 |
| Second Round | Hugo Gaston | Win | 7-6 (7-4), 6-4, 6-4 |
| Third Round | Rafael Nadal | Loss | 1-6, 2-6, 4-6 |
| Rothesay International Eastbourne | ||
| Surface: Grass | Date: Jun. 19 - Jun. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | James Duckworth | Win | 4-6, 7-6 (7-5), 7-6 (7-1) |
| Second Round | Alex De Minaur | Loss | 6-7 (3-7), 2-6 |
| cinch Championships | ||
| Surface: Grass | Date: Jun. 13 - Jun. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Denis Kudla | Loss | 4-6, 6-3, 4-6 |
| BOSS OPEN | ||
| Surface: Grass | Date: Jun. 6 - Jun. 12 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Benoit Paire | Win | 7-5, 6-2 |
| Second Round | Jan-Lennard Struff | Win | 7-6 (7-2), 7-6 (7-4) |
| Quarterfinals | Matteo Berrettini | Loss | 6-3, 3-6, 4-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 22 - Jun. 5 | Seed: 32 |
| Round | Opponent | W / L | Result |
| First Round | Peter Gojowczyk | Win | 6-2, 6-2, 6-1 |
| Second Round | Joao Sousa | Win | 7-6 (7-4), 6-3, 6-4 |
| Third Round | Casper Ruud | Loss | 2-6, 7-6 (7-3), 6-1, 4-6, 3-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 8 - May 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Denis Shapovalov | Loss | 6-7 (5-7), 6-3, 3-6 |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 28 - May 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jack Draper | Loss | 4-6, 3-6 |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 18 - Apr. 24 | Seed: 11 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Elias Ymer | Win | 6-4, 6-2 |
| Third Round | Pablo Carreno Busta | Loss | 2-6, 7-5, 2-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 10 - Apr. 17 | Seed: 16 |
| Round | Opponent | W / L | Result |
| First Round | Ilya Ivashka | Win | 6-3, 6-3 |
| Second Round | Laslo Djere | Loss | 4-6, 4-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 3 | Seed: 19 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Denis Kudla | Loss | 6-3, 6-7 (5-7), 4-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 9 - Mar. 20 | Seed: 21 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Benjamin Bonzi | Loss | 3-6, 4-6 |
| Abierto Mexicano Telcel presentado por HSBC | ||
| Surface: Hard | Date: Feb. 21 - Feb. 26 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | J.J. Wolf | Loss | 6-3, 6-7 (7-9), 2-6 |
| Rio Open presented by Claro HDTV | ||
| Surface: Clay | Date: Feb. 14 - Feb. 20 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Laslo Djere | Win | 6-2, 6-0 |
| Second Round | Miomir Kecmanovic | Loss | 5-7, 4-6 |
| Argentina Open | ||
| Surface: Clay | Date: Feb. 7 - Feb. 13 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Sebastian Baez | Win | 6-3, 6-3 |
| Quarterfinals | Fernando Verdasco | Win | 6-4, 7-6 (7-4) |
| Semifinals | Diego Schwartzman | Loss | 5-7, 6-3, 2-6 |
| Cordoba Open | ||
| Surface: Red Clay | Date: Jan. 31 - Feb. 6 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Roberto Carballes Baena | Win | 4-6, 7-6 (7-1), 6-2 |
| Quarterfinals | Albert Ramos-Vinolas | Loss | 6-7 (5-7), 5-7 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 17 - Jan. 30 | Seed: 25 |
| Round | Opponent | W / L | Result |
| First Round | Sam Querrey | Win | 7-5, 6-3, 6-3 |
| Second Round | Oscar Otte | Win | 2-6, 6-2, 6-3, 6-1 |
| Third Round | Miomir Kecmanovic | Loss | 4-6, 7-6 (10-8), 2-6, 5-7 |
| Sydney Tennis Classic | ||
| Surface: Hard | Date: Jan. 10 - Jan. 15 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Hugo Gaston | Win | 3-6, 6-3, 7-5 |
| Second Round | Sebastian Baez | Win | 6-2, 6-3 |
| Quarterfinals | Aslan Karatsev | Loss | 2-6, 6-3, 2-6 |
