| ||||||||||||||
| VTB Kremlin Cup | ||
| Surface: Hard | Date: Oct. 18 - Oct. 24 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Damir Dzumhur | Win | 6-7 (4-7), 6-1, 6-1 |
| Second Round | Tommy Paul | Win | 7-5, 6-3 |
| Quarterfinals | Pedro Martinez |
| US Open | ||
| Surface: Hard | Date: Aug. 30 - Sep. 12 | Seed: 30 |
| Round | Opponent | W / L | Result |
| First Round | Philipp Kohlschreiber | Loss | 7-6 (7-4), 7-6 (7-3), 2-6, 1-6, 0-2 Retired |
| Winston-Salem Open | ||
| Surface: Hard | Date: Aug. 22 - Aug. 28 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Ilya Ivashka | Loss | 6-4, 5-7, 4-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 15 - Aug. 22 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Aslan Karatsev | Win | 7-5, 6-3 |
| Second Round | Andrey Rublev | Loss | 7-5, 3-6, 1-6 |
| Open de la Banque Nationale presentee par Rogers | ||
| Surface: Hard | Date: Aug. 9 - Aug. 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Albert Ramos-Vinolas | Win | 6-2, 4-6, 6-3 |
| Second Round | Casper Ruud | Loss | 3-6, 6-3, 3-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 28 - Jul. 11 | Seed: 32 |
| Round | Opponent | W / L | Result |
| First Round | Salvatore Caruso | Win | 7-6 (7-5), 7-6 (7-1), 6-1 |
| Second Round | Benjamin Bonzi | Win | 6-4, 3-6, 6-3, 7-6(7-5) |
| Third Round | Daniil Medvedev | Loss | 7-6 (7-3), 6-3, 3-6, 3-6, 2-6 |
| cinch Championships | ||
| Surface: Grass | Date: Jun. 14 - Jun. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Sebastian Ofner | Win | 6-2, 6-7 (5-7), 7-6 (7-4) |
| Second Round | Fabio Fognini | Win | 6-3, 7-6 (7-4) |
| Quarterfinals | Alex De Minaur | Loss | 6-3, 3-6, 4-6 |
| MercedesCup | ||
| Surface: Grass | Date: Jun. 8 - Jun. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Rudolf Molleker | Win | 7-5, 6-3 |
| Second Round | Nikoloz Basilashvili | Win | 6-3, 6-2 |
| Quarterfinals | Denis Shapovalov | Win | 7-5, 7-6 (7-3) |
| Semifinals | Jurij Rodionov | Win | 6-3, 1-0 Retired |
| Final | Felix Auger-Aliassime | Win | 7-6 (7-2), 6-3 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 30 - Jun. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Arthur Rinderknech | Win | 7-6 (8-6), 6-1, 6-2 |
| Second Round | Roger Federer | Loss | 2-6, 6-2, 6-7 (4-7), 2-6 |
| Gonet Geneva Open | ||
| Surface: Clay | Date: May 16 - May 22 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Dominic Stephan Stricker | Loss | 6-7 (5-7), 1-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 9 - May 16 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alexander Bublik | Win | 4-6, 6-2, 6-3 |
| Second Round | Stefanos Tsitsipas | Loss | 5-7, 2-6 |
| Millennium Estoril Open | ||
| Surface: Red Clay | Date: Apr. 26 - May 2 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Carlos Alcaraz | Win | 6-3, 1-6, 6-4 |
| Second Round | Nuno Borges | Win | 6-7 (5-7), 6-4, 6-4 |
| Quarterfinals | Kevin Anderson | Win | 7-6 (9-7), 0-0 Retired |
| Semifinals | Cameron Norrie | Loss | 6-7 (5-7), 5-7 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 11 - Apr. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | David Goffin | Loss | 4-6, 6-3, 0-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 23 - Apr. 4 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Federico Coria | Win | 6-3, 2-6, 6-4 |
| Second Round | Cristian Garin | Win | 3-6, 7-5, 7-6 (7-5) |
| Third Round | Lorenzo Musetti | Win | 6-3, 6-4 |
| Fourth Round | Andrey Rublev | Loss | 4-6, 4-6 |
| Abierto Mexicano Telcel presentado por HSBC | ||
| Surface: Hard | Date: Mar. 15 - Mar. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Sebastian Korda | Loss | 5-7, 2-6 |
| Singapore Tennis Open | ||
| Surface: Hard | Date: Feb. 22 - Feb. 28 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Taro Daniel | Win | 7-5, 6-4 |
| Quarterfinals | Soon Woo Kwon | Win | 6-2, 2-6, 7-5 |
| Semifinals | Alexei Popyrin | Loss | 6-7 (5-7), 6-7 (2-7) |
| Australian Open | ||
| Surface: Hard | Date: Feb. 8 - Feb. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Grigor Dimitrov | Loss | 4-6, 2-6, 6-7 (5-7) |
| Murray River Open | ||
| Surface: Hard | Date: Feb. 1 - Feb. 7 | Seed: 11 |
| Round | Opponent | W / L | Result |
| First Round | Jeremy Chardy | Loss | 6-2, 3-6, 6-7 (8-10) |
© 2021 by STATS PERFORM.Any commercial use or distribution without the express written consent of STATS PERFORM is strictly prohibited.