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| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 14 - Aug. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jenson Brooksby | Win | 6-3, 6-2 |
| Second Round | Denis Shapovalov | Loss | 6-3, 4-6, 3-6 |
| Open de la Banque Nationale presentee par Rogers | ||
| Surface: Hard | Date: Aug. 8 - Aug. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Vasek Pospisil | Win | 6-4, 6-4 |
| Second Round | Carlos Alcaraz | Win | 6-7 (4-7), 7-6 (9-7), 6-3 |
| Third Round | Marin Cilic | Win | 6-4, 6-2 |
| Quarterfinals | Daniel Evans | Loss | 6-1, 3-6, 4-6 |
| Citi Open | ||
| Surface: Hard | Date: Aug. 1 - Aug. 7 | Seed: 14 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Nick Kyrgios | Loss | 3-6, 4-6 |
| Atlanta Open | ||
| Surface: Hard | Date: Jul. 25 - Jul. 31 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Jack Sock | Win | 6-1, 6-1 |
| Second Round | Soon Woo Kwon | Win | 6-3, 6-3 |
| Quarterfinals | Ilya Ivashka | Loss | 2-6, 6-3, 1-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 27 - Jul. 10 | Seed: 30 |
| Round | Opponent | W / L | Result |
| First Round | Fernando Verdasco | Win | 6-1, 6-2, 7-6 (7-4) |
| Second Round | Adrian Mannarino | Win | 6-2, 6-4, 6-1 |
| Third Round | Jiri Vesely | Win | 6-3, 6-2, 6-2 |
| Fourth Round | Cameron Norrie | Loss | 4-6, 5-7, 4-6 |
| Rothesay International Eastbourne | ||
| Surface: Grass | Date: Jun. 19 - Jun. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Francisco Cerundolo | Win | 4-6, 7-6 (7-2), 6-4 |
| Second Round | Jannik Sinner | Win | 6-3, 3-6, 6-3 |
| Quarterfinals | Alex De Minaur | Loss | 2-6, 6-4, 4-6 |
| cinch Championships | ||
| Surface: Grass | Date: Jun. 13 - Jun. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Denis Shapovalov | Win | 6-4, 2-6, 6-4 |
| Second Round | Stan Wawrinka | Win | 6-1, 6-4 |
| Quarterfinals | Matteo Berrettini | Loss | 4-6, 2-6 |
| Libema Open | ||
| Surface: Grass | Date: Jun. 6 - Jun. 12 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Brandon Nakashima | Loss | 7-6 (7-4), 6-7 (5-7), 6-7 (2-7) |
| Roland Garros | ||
| Surface: Red Clay | Date: May 22 - Jun. 5 | Seed: 30 |
| Round | Opponent | W / L | Result |
| First Round | Cristian Garin | Loss | 7-5, 1-6, 2-6, 3-6 |
| Gonet Geneva Open | ||
| Surface: Clay | Date: May 15 - May 21 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Tallon Griekspoor | Loss | 5-7, 7-6 (7-3), 4-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 8 - May 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Albert Ramos-Vinolas | Win | 6-4, 6-4 |
| Second Round | Alex De Minaur | Loss | 5-7, 4-6 |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 28 - May 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jannik Sinner | Loss | 7-6 (7-4), 6-7 (4-7), 3-6 |
| Millennium Estoril Open | ||
| Surface: Red Clay | Date: Apr. 25 - May 1 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Richard Gasquet | Loss | 5-7, 2-6 |
| Fayez Sarofim & Co. US Men's Clay Court Championship | ||
| Surface: Clay | Date: Apr. 4 - Apr. 10 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Peter Gojowczyk | Win | 6-7 (4-7), 7-6 (7-5), 3-2 Retired |
| Second Round | Nick Kyrgios | Loss | 4-6, 2-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 3 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Benjamin Bonzi | Win | 6-4, 6-4 |
| Second Round | Karen Khachanov | Win | 6-4, 3-6, 7-6 (7-3) |
| Third Round | Taylor Fritz | Loss | 6-7 (2-7), 4-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 9 - Mar. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Mikhail Kukushkin | Win | 6-4, 6-4 |
| Second Round | Alexander Zverev | Win | 6-2, 4-6, 7-6 (7-2) |
| Third Round | Alex De Minaur | Loss | 6-7 (2-7), 4-6 |
| Abierto Mexicano Telcel presentado por HSBC | ||
| Surface: Hard | Date: Feb. 21 - Feb. 26 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Matteo Berrettini | Win | 4-6, 5-1 Retired |
| Second Round | Dusan Lajovic | Win | 7-6 (8-6), 2-6, 7-5 |
| Quarterfinals | Rafael Nadal | Loss | 0-6, 6-7 (5-7) |
| Delray Beach Open by VITACOST.com | ||
| Surface: Hard | Date: Feb. 14 - Feb. 20 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Denis Istomin | Win | 6-2, 6-0 |
| Quarterfinals | Stefan Kozlov | Win | 6-3, 6-1 |
| Semifinals | Cameron Norrie | Loss | 3-6, 3-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 17 - Jan. 30 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Mikhail Kukushkin | Win | 6-3, 6-4, 6-2 |
| Second Round | Miomir Kecmanovic | Loss | 6-7 (7-9), 5-7, 6-7 (8-10) |
| Adelaide International 2 | ||
| Surface: Hard | Date: Jan. 10 - Jan. 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Frances Tiafoe | Win | 6-2, 6-3 |
| Second Round | Benjamin Bonzi | Win | 6-4, 7-6 (8-6) |
| Quarterfinals | Marin Cilic | Loss | 4-6, 6-2, 3-6 |
| Adelaide International 1 | ||
| Surface: Hard | Date: Jan. 3 - Jan. 9 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Jiri Vesely | Win | 6-4, 4-6, 6-4 |
| Second Round | Taro Daniel | Win | 6-4, 6-7 (1-7), 6-4 |
| Quarterfinals | Gael Monfils | Loss | 4-6, 1-6 |
