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| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 14 - Aug. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | David Goffin | Win | 6-3, 6-4 |
| Second Round | Roberto Bautista Agut | Loss | 3-6, 3-6 |
| Open de la Banque Nationale presentee par Rogers | ||
| Surface: Hard | Date: Aug. 8 - Aug. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Roberto Bautista Agut | Loss | 6-7 (5-7), 3-6 |
| Citi Open | ||
| Surface: Hard | Date: Aug. 1 - Aug. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nick Kyrgios | Loss | 3-6, 2-6 |
| Atlanta Open | ||
| Surface: Hard | Date: Jul. 25 - Jul. 31 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Soon Woo Kwon | Loss | 6-7 (3-7), 6-4, 5-7 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 27 - Jul. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Holger Rune | Win | 6-3, 7-5, 6-4 |
| Second Round | Alex Molcan | Loss | 3-6, 2-6, 4-6 |
| Mallorca Championships | ||
| Surface: Grass | Date: Jun. 19 - Jun. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Botic van de Zandschulp | Win | 6-7 (6-8), 6-4, 7-6 (7-2) |
| Second Round | Mackenzie McDonald | Win | 4-6, 7-6 (7-5), 6-4 |
| Quarterfinals | Stefanos Tsitsipas | Loss | 6-7 (5-7), 6-4, 3-6 |
| Terra Wortmann Open | ||
| Surface: Grass | Date: Jun. 13 - Jun. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Felix Auger-Aliassime | Loss | 3-6, 7-5, 3-6 |
| BOSS OPEN | ||
| Surface: Grass | Date: Jun. 6 - Jun. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jan-Lennard Struff | Loss | 5-7, 7-5, 6-7 (8-10) |
| Roland Garros | ||
| Surface: Red Clay | Date: May 22 - Jun. 5 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Grigor Dimitrov | Loss | 1-6, 1-6, 1-6 |
| Gonet Geneva Open | ||
| Surface: Clay | Date: May 15 - May 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ilya Ivashka | Loss | 6-4, 3-6, 2-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 8 - May 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alexander Bublik | Win | 3-6, 6-4, 6-3 |
| Second Round | Diego Schwartzman | Win | 6-1, 7-6 (7-4) |
| Third Round | Felix Auger-Aliassime | Loss | 3-6, 2-6 |
| BMW Open by American Express | ||
| Surface: Red Clay | Date: Apr. 25 - May 1 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Hugo Gaston | Loss | 4-6, 7-6 (7-4), 5-7 |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 18 - Apr. 24 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Federico Coria | Loss | 2-6, 6-3, 1-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 10 - Apr. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alejandro Davidovich Fokina | Loss | 5-7, 3-6 |
| Fayez Sarofim & Co. US Men's Clay Court Championship | ||
| Surface: Clay | Date: Apr. 4 - Apr. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Frances Tiafoe | Loss | 4-6, 4-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 3 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marton Fucsovics | Loss | 3-6, 4-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 9 - Mar. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Lorenzo Musetti | Loss | 3-6, 5-7 |
| Abierto Mexicano Telcel presentado por HSBC | ||
| Surface: Hard | Date: Feb. 21 - Feb. 26 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | John Millman | Win | 7-6 (7-3), 2-0 Retired |
| Second Round | Pablo Carreno Busta | Win | 6-7 (7-9), 6-4, 7-6 (7-4) |
| Quarterfinals | Stefanos Tsitsipas | Loss | 3-6, 4-6 |
| Delray Beach Open by VITACOST.com | ||
| Surface: Hard | Date: Feb. 14 - Feb. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Tennys Sandgren | Win | 7-5, 6-3 |
| Second Round | John Millman | Loss | 3-6, 6-7 (6-8) |
| Dallas Open | ||
| Surface: Hard | Date: Feb. 7 - Feb. 13 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Tennys Sandgren | Win | 6-4, 6-4 |
| Second Round | Liam Broady | Win | 3-6, 6-3, 6-1 |
| Quarterfinals | Taylor Fritz | Win | 6-4, 3-6, 7-6 (7-3) |
| Semifinals | Jenson Brooksby | Loss | 4-6, 7-6 (7-4), 6-7 (5-7) |
| Australian Open | ||
| Surface: Hard | Date: Jan. 17 - Jan. 30 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Rafael Nadal | Loss | 1-6, 4-6, 2-6 |
| Sydney Tennis Classic | ||
| Surface: Hard | Date: Jan. 10 - Jan. 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jordan Thompson | Loss | 4-6, 2-6 |
| Melbourne Summer Set 1 | ||
| Surface: Hard | Date: Jan. 4 - Jan. 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ricardas Berankis | Loss | 5-7, 4-6 |
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