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| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 14 - Aug. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Aslan Karatsev | Loss | 5-7, 5-7 |
| Open de la Banque Nationale presentee par Rogers | ||
| Surface: Hard | Date: Aug. 8 - Aug. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Cameron Norrie | Loss | 4-6, 4-6 |
| Abierto de Tenis Mifel | ||
| Surface: Hard | Date: Aug. 1 - Aug. 6 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Kaichi Uchida | Win | 7-6 (7-1), 6-2 |
| Second Round | Max Purcell | Win | 6-3, 6-3 |
| Quarterfinals | Miomir Kecmanovic | Loss | 2-6, 4-6 |
| Atlanta Open | ||
| Surface: Hard | Date: Jul. 25 - Jul. 31 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Jordan Thompson | Win | 7-6 (7-5), 3-6, 6-3 |
| Second Round | John Millman | Win | 7-6 (10-8), 6-4 |
| Quarterfinals | Frances Tiafoe | Loss | 4-6, 2-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 27 - Jul. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nicola Kuhn | Win | 6-3, 6-7 (1-7), 6-3, 6-2 |
| Second Round | Denis Shapovalov | Win | 6-2, 4-6, 6-1, 7-6(8-6) |
| Third Round | Daniel Elahi Galan | Win | 6-4, 6-4, 6-1 |
| Fourth Round | Nick Kyrgios | Loss | 6-4, 4-6, 6-7 (2-7), 6-3, 2-6 |
| Rothesay International Eastbourne | ||
| Surface: Grass | Date: Jun. 19 - Jun. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jay Clarke | Win | 6-1, 6-3 |
| Second Round | Cameron Norrie | Loss | 4-6, 2-6 |
| Libema Open | ||
| Surface: Grass | Date: Jun. 6 - Jun. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Tommy Paul | Win | 6-7 (4-7), 7-6 (7-5), 7-6 (7-2) |
| Second Round | Sam Querrey | Win | 7-6 (7-4), 7-6 (8-6) |
| Quarterfinals | Adrian Mannarino | Loss | 7-6 (7-5), 1-6, 4-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 22 - Jun. 5 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Kamil Majchrzak | Win | 6-4, 2-6, 4-6, 7-6(7-3), 6-2 |
| Second Round | Tallon Griekspoor | Win | 7-6 (8-6), 6-4, 6-2 |
| Third Round | Alexander Zverev | Loss | 6-7 (2-7), 3-6, 6-7 (5-7) |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 8 - May 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Grigor Dimitrov | Loss | 3-6, 4-6 |
| BMW Open by American Express | ||
| Surface: Red Clay | Date: Apr. 25 - May 1 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Botic van de Zandschulp | Loss | 6-7 (3-7), 3-6 |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 18 - Apr. 24 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nicolas Alvarez Varona | Win | 7-6 (8-6), 6-3 |
| Second Round | Casper Ruud | Loss | 3-6, 2-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 3 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Soon Woo Kwon | Win | 6-1, 7-5 |
| Second Round | Frances Tiafoe | Loss | 6-3, 6-7 (5-7), 4-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 9 - Mar. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Adrian Mannarino | Win | 6-2, 7-6 (7-4) |
| Second Round | Frances Tiafoe | Loss | 4-6, 4-6 |
| Abierto Mexicano Telcel presentado por HSBC | ||
| Surface: Hard | Date: Feb. 21 - Feb. 26 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Peter Gojowczyk | Loss | 4-6, 4-6 |
| Delray Beach Open by VITACOST.com | ||
| Surface: Hard | Date: Feb. 14 - Feb. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Denis Kudla | Win | 6-1, 6-1 |
| Second Round | Adrian Mannarino | Loss | 4-6, 6-2, 5-7 |
| Dallas Open | ||
| Surface: Hard | Date: Feb. 7 - Feb. 13 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | John Millman | Win | 7-5, 7-6 (7-3) |
| Second Round | Jordan Thompson | Loss | 5-7, 6-7 (1-7) |
| Australian Open | ||
| Surface: Hard | Date: Jan. 17 - Jan. 30 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Matteo Berrettini | Loss | 6-4, 2-6, 6-7 (5-7), 3-6 |
| Sydney Tennis Classic | ||
| Surface: Hard | Date: Jan. 10 - Jan. 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jiri Vesely | Win | 7-6 (7-2), 7-6 (7-0) |
| Second Round | Fabio Fognini | Win | 7-6 (9-7), 7-6 (8-6) |
| Quarterfinals | Reilly Opelka | Loss | 6-7 (4-7), 2-6 |
