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| US Open | ||
| Surface: Hard | Date: Aug. 28 - Sep. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Aslan Karatsev | Loss | 3-6, 3-6, 3-6 |
| Winston-Salem Open | ||
| Surface: Hard | Date: Aug. 20 - Aug. 26 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Mitchell Krueger | Win | 2-6, 6-2, 6-3 |
| Third Round | Dominik Koepfer | Win | 6-3, 3-6, 6-4 |
| Quarterfinals | Max Purcell | Win | 7-6 (7-4), 6-4 |
| Semifinals | Sebastian Korda | Win | |
| Final | Sebastian Baez | Loss | 4-6, 3-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 13 - Aug. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Taylor Fritz | Loss | 6-7 (14-16), 2-6 |
| Omnium National Bank presented by Rogers | ||
| Surface: Hard | Date: Aug. 7 - Aug. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Brandon Nakashima | Win | 7-5, 3-6, 7-6 (7-2) |
| Second Round | Casper Ruud | Loss | 6-7 (6-8), 4-6 |
| Plava Laguna Croatia Open Umag | ||
| Surface: Red Clay | Date: Jul. 24 - Jul. 30 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Dominic Thiem | Win | 6-3, 7-5 |
| Quarterfinals | Matteo Arnaldi | Loss | 6-3, 2-6, 4-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 3 - Jul. 16 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Sebastian Ofner | Win | |
| Second Round | Francisco Cerundolo | Win | |
| Third Round | Tommy Paul | Win | |
| Fourth Round | Daniil Medvedev | Loss |
| Cinch Championships | ||
| Surface: Grass | Date: Jun. 19 - Jun. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alejandro Davidovich Fokina | Win | |
| Second Round | Carlos Alcaraz | Loss |
| Boss Open | ||
| Surface: Grass | Date: Jun. 12 - Jun. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marcos Giron | Win | |
| Second Round | Frances Tiafoe | Loss |
| French Open | ||
| Surface: Red Clay | Date: May 28 - Jun. 11 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jan-Lennard Struff | Win | |
| Second Round | Marcos Giron | Loss |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 10 - May 21 | Seed: 32 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Fabian Marozsan | Loss |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 26 - May 7 | Seed: 31 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Alexander Shevchenko | Loss |
| Banja Luka Open | ||
| Surface: Clay | Date: Apr. 17 - Apr. 23 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Gael Monfils | Win | |
| Second Round | Radu Albot | Win | |
| Quarterfinals | Miomir Kecmanovic | Loss |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 9 - Apr. 16 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Emil Ruusuvuori | Win | |
| Second Round | Grigor Dimitrov | Win | |
| Third Round | Taylor Fritz | Loss |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 2 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Federico Coria | Win | |
| Second Round | Lorenzo Musetti | Win | |
| Third Round | Karen Khachanov | Loss |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 8 - Mar. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Arthur Rinderknech | Win | |
| Second Round | Andrey Rublev | Loss |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 27 - Mar. 4 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alexander Zverev | Loss |
| Qatar ExxonMobil Open | ||
| Surface: Hard | Date: Feb. 20 - Feb. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Damir Dzumhur | Win | |
| Second Round | Emil Ruusuvuori | Win | |
| Quarterfinals | Andrey Rublev | Win | |
| Semifinals | Andy Murray | Loss |
| Australian Open | ||
| Surface: Hard | Date: Jan. 15 - Jan. 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Borna Coric | Win | |
| Second Round | Christopher Eubanks | Win | |
| Third Round | Cameron Norrie | Win | |
| Fourth Round | Felix Auger-Aliassime | Win | |
| Quarterfinals | Stefanos Tsitsipas | Loss |
| ASB Classic | ||
| Surface: Hard | Date: Jan. 9 - Jan. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Thiago Monteiro | Win | |
| Second Round | Cameron Norrie | Loss |
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