| ||||||||||||||
| Sofia Open | ||
| Surface: Hard | Date: Sep. 26 - Oct. 2 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Aleksandar Vukic | Loss | 6-7 (11-13), 5-7 |
| US Open | ||
| Surface: Hard | Date: Aug. 29 - Sep. 11 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Aslan Karatsev | Win | 1-6, 5-7, 6-4, 6-1, 6-4 |
| Second Round | Rafael Nadal | Loss | 6-2, 4-6, 2-6, 1-6 |
| Winston-Salem Open | ||
| Surface: Hard | Date: Aug. 21 - Aug. 27 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Dusan Lajovic | Win | |
| Second Round | Jack Draper | Loss |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 14 - Aug. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Albert Ramos-Vinolas | Win | |
| Second Round | Andrey Rublev | Loss |
| Open de la Banque Nationale presentee par Rogers | ||
| Surface: Hard | Date: Aug. 8 - Aug. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Holger Rune | Loss |
| Plava Laguna Croatia Open Umag | ||
| Surface: Clay | Date: Jul. 25 - Jul. 31 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Daniel Elahi Galan | Loss |
| Hamburg European Open | ||
| Surface: Red Clay | Date: Jul. 17 - Jul. 24 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Aljaz Bedene | Win | |
| Second Round | Karen Khachanov | Loss |
| Nordea Open | ||
| Surface: Clay | Date: Jul. 11 - Jul. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Sebastian Baez | Loss |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 27 - Jul. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Tallon Griekspoor | Loss |
| Roland Garros | ||
| Surface: Red Clay | Date: May 22 - Jun. 5 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alexei Popyrin | Win | |
| Second Round | Botic van de Zandschulp | Loss |
| Gonet Geneva Open | ||
| Surface: Clay | Date: May 15 - May 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Thanasi Kokkinakis | Loss |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 8 - May 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Dominic Thiem | Win | |
| Second Round | Jannik Sinner | Loss |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 28 - May 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nikoloz Basilashvili | Loss |
| Serbia Open | ||
| Surface: Red Clay | Date: Apr. 18 - Apr. 24 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Marco Cecchinato | Win | |
| Second Round | Aljaz Bedene | Win | |
| Quarterfinals | Oscar Otte | Win | |
| Semifinals | Andrey Rublev | Loss |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 10 - Apr. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Arthur Rinderknech | Win | |
| Second Round | Stefanos Tsitsipas | Loss |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 3 | Seed: 31 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Taro Daniel | Win | |
| Third Round | Nick Kyrgios | Loss |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 9 - Mar. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Pablo Andujar | Win | |
| Second Round | Nikoloz Basilashvili | Loss |
| Rio Open presented by Claro HDTV | ||
| Surface: Clay | Date: Feb. 14 - Feb. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Facundo Bagnis | Win | |
| Second Round | Pablo Carreno Busta | Win | |
| Quarterfinals | Federico Coria | Win | |
| Semifinals | Carlos Alcaraz | Loss |
| Argentina Open | ||
| Surface: Clay | Date: Feb. 7 - Feb. 13 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Pedro Martinez | Win | |
| Quarterfinals | Federico Delbonis | Loss |
| Australian Open | ||
| Surface: Hard | Date: Jan. 17 - Jan. 30 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Tallon Griekspoor | Loss |
| Sydney Tennis Classic | ||
| Surface: Hard | Date: Jan. 10 - Jan. 15 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Daniel Altmaier | Win | |
| Second Round | Brandon Nakashima | Loss |
