Sports News
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| VTB Kremlin Cup | ||
| Surface: Hard | Date: Oct. 18 - Oct. 24 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Roman Safiullin |
| BNP Paribas Open | ||
| Surface: Hard | Date: Oct. 6 - Oct. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Andy Murray | Loss | 3-6, 2-6 |
| Sofia Open | ||
| Surface: Hard | Date: Sep. 27 - Oct. 3 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Gianluca Mager | Loss | 3-6, 2-6 |
| US Open | ||
| Surface: Hard | Date: Aug. 30 - Sep. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Pierre-Hugues Herbert | Win | 3-6, 4-6, 6-4, 6-3, 6-3 |
| Second Round | Stefanos Tsitsipas | Loss | 3-6, 4-6, 7-6 (7-4), 0-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 28 - Jul. 11 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Roger Federer | Loss | 4-6, 7-6 (7-3), 6-3, 2-6 Retired |
| Mallorca Championships | ||
| Surface: Grass | Date: Jun. 20 - Jun. 26 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jan-Lennard Struff | Win | 7-6 (7-3), 6-3 |
| Second Round | Dominic Thiem | Win | 2-5 Retired |
| Quarterfinals | Feliciano Lopez | Win | 6-4, 3-6, 6-3 |
| Semifinals | Sam Querrey | Loss | 4-6, 3-6 |
| cinch Championships | ||
| Surface: Grass | Date: Jun. 14 - Jun. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Liam Broady | Win | 6-4, 6-4 |
| Second Round | Daniel Evans | Loss | 4-6, 6-7 (7-9) |
| MercedesCup | ||
| Surface: Grass | Date: Jun. 8 - Jun. 13 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | James Duckworth | Loss | 3-6, 2-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 30 - Jun. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Aljaz Bedene | Loss | 5-7, 6-3, 5-7, 2-6 |
| Gonet Geneva Open | ||
| Surface: Clay | Date: May 16 - May 22 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Arthur Cazaux | Loss | 3-6, 7-6 (7-5), 3-6 |
| Serbia Open | ||
| Surface: Red Clay | Date: May 16 - May 29 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Fernando Verdasco | Loss | 6-7 (4-7), 0-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 9 - May 16 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Hugo Dellien | Loss | 6-2, 5-7, 2-6 |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 29 - May 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Carlos Alcaraz | Loss | 4-6, 0-6 |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 19 - Apr. 25 | Seed: 17 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Albert Ramos-Vinolas | Loss | 4-6, 4-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 11 - Apr. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Federico Delbonis | Loss | 5-7, 1-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 23 - Apr. 4 | Seed: 25 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Miomir Kecmanovic | Win | 6-3, 6-4 |
| Third Round | Diego Schwartzman | Loss | 1-6, 4-6 |
| Abierto Mexicano Telcel presentado por HSBC | ||
| Surface: Hard | Date: Mar. 15 - Mar. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Grigor Dimitrov | Loss | 4-6, 0-3 Retired |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Mar. 1 - Mar. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Hubert Hurkacz | Loss | 3-6, 6-7 (6-8) |
| Singapore Tennis Open | ||
| Surface: Hard | Date: Feb. 22 - Feb. 28 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Roberto Marcora | Win | 6-3, 7-5 |
| Quarterfinals | Radu Albot | Loss | 3-6, 4-6 |
| Australian Open | ||
| Surface: Hard | Date: Feb. 8 - Feb. 21 | Seed: 32 |
| Round | Opponent | W / L | Result |
| First Round | Dennis Novak | Win | 6-2, 6-4, 7-6 (7-2) |
| Second Round | Miomir Kecmanovic | Win | 6-1, 6-2, 6-4 |
| Third Round | Alexander Zverev | Loss | 3-6, 3-6, 1-6 |
| Murray River Open | ||
| Surface: Hard | Date: Feb. 1 - Feb. 7 | Seed: 10 |
| Round | Opponent | W / L | Result |
| First Round | Mikael Ymer | Win | 7-5, 6-2 |
| Second Round | Marcos Giron | Loss | 3-6, 4-6 |
| Delray Beach Open by VITACOST.com | ||
| Surface: Hard | Date: Jan. 7 - Jan. 13 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Cameron Norrie | Loss | 2-6, 5-7 |
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