| ||||||||||||||
| St. Petersburg Open | ||
| Surface: Hard | Date: Sep. 17 - Sep. 23 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Denis Istomin | Win | 7-5, 2-4 Retired |
| Second Round | Daniil Medvedev | Loss | 3-6, 4-6 |
| US Open | ||
| Surface: Hard | Date: Aug. 27 - Sep. 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Noah Rubin | Win | 6-3, 6-1, 4-6, 7-6(7-3) |
| Second Round | Hyeon Chung | Win | 7-6 (7-5), 6-2, 6-3 |
| Third Round | John Millman | Loss | 4-6, 6-4, 1-6, 3-6 |
| Generali Open | ||
| Surface: Clay | Date: Jul. 30 - Aug. 4 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Corentin Moutet | Win | 4-6, 6-3, 6-4 |
| Second Round | Maximilian Marterer | Loss | 3-6, 4-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 2 - Jul. 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Vasek Pospisil | Win | 6-4, 3-6, 6-2, 6-3 |
| Second Round | Rafael Nadal | Loss | 4-6, 3-6, 4-6 |
| Nature Valley International | ||
| Surface: Grass | Date: Jun. 24 - Jun. 30 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alex De Minaur | Win | 6-1, 6-2 |
| Second Round | David Ferrer | Win | 6-2, 6-0 |
| Quarterfinals | Kyle Edmund | Win | 5-7, 6-3, 6-1 |
| Semifinals | Mischa Zverev | Loss | 6-7 (9-11), 4-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 27 - Jun. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Albert Ramos-Vinolas | Loss | 6-7 (0-7), 4-6, 1-6 |
| Open Parc Auvergne-Rhone-Alpes Lyon | ||
| Surface: Clay | Date: May 20 - May 26 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Gregoire Barrere | Win | 6-2, 6-3 |
| Second Round | Federico Coria | Win | 6-2, 6-3 |
| Quarterfinals | Gilles Simon | Loss | 6-4, 4-6, 6-7 (5-7) |
| Mutua Madrid Open | ||
| Surface: Red Clay | Date: May 5 - May 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Roberto Carballes Baena | Win | 6-3, 6-2 |
| Second Round | Kevin Anderson | Loss | 7-5, 6-7 (3-7), 2-6 |
| BMW Open by FWU | ||
| Surface: Red Clay | Date: Apr. 30 - May 6 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Matthias Bachinger | Loss | 6-7 (8-10), 6-3, 3-6 |
| Barcelona Open Banco Sabadell | ||
| Surface: Clay | Date: Apr. 23 - Apr. 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marcel Granollers | Loss | 2-6, 2-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 20 - Apr. 1 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marius Copil | Loss | 6-7 (2-7), 4-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 7 - Mar. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Mischa Zverev | Loss | 3-6, 6-4, 1-6 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 26 - Mar. 3 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Stefanos Tsitsipas | Loss | 2-6, 7-6 (7-5), 3-6 |
| Open 13 Marseille | ||
| Surface: Hard | Date: Feb. 19 - Feb. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Damir Dzumhur | Loss | 7-6 (8-6), 6-7 (3-7), 1-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 15 - Jan. 28 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Peter Gojowczyk | Loss | 3-6, 3-6, 1-6 |
| Tata Open Maharashtra | ||
| Surface: Hard | Date: Jan. 1 - Jan. 6 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Radu Albot | Win | 6-2, 7-6 (7-4) |
| Second Round | Laslo Djere | Win | 7-5, 7-6 (7-5) |
| Quarterfinals | Kevin Anderson | Loss | 7-6 (7-3), 4-6, 2-6 |
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