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| US Open | ||
| Surface: Hard | Date: Aug. 30 - Sep. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Christopher Eubanks | Win | 7-6 (10-8), 5-7, 6-3, 6-4 |
| Second Round | Guido Pella | Win | 6-1, 6-2, 7-5 |
| Third Round | Andrey Rublev | Win | 4-6, 6-3, 7-6 (8-6), 4-6, 6-1 |
| Fourth Round | Felix Auger-Aliassime | Loss | 6-4, 2-6, 6-7 (6-8), 4-6 |
| Winston-Salem Open | ||
| Surface: Hard | Date: Aug. 22 - Aug. 28 | Seed: 13 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Andy Murray | Win | 7-6 (7-4), 6-3 |
| Third Round | Thiago Monteiro | Win | 7-5, 7-6 (7-2) |
| Quarterfinals | Mikael Ymer | Loss | 7-6 (7-2), 2-6, 3-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 15 - Aug. 22 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ugo Humbert | Win | 7-5, 7-6 (11-9) |
| Second Round | Diego Schwartzman | Loss | 1-6, 6-4, 4-6 |
| Open de la Banque Nationale presentee par Rogers | ||
| Surface: Hard | Date: Aug. 9 - Aug. 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Yoshihito Nishioka | Win | 6-4, 6-3 |
| Second Round | Denis Shapovalov | Win | 6-1, 6-4 |
| Third Round | Gael Monfils | Loss | 1-6, 6-7 (2-7) |
| Citi Open | ||
| Surface: Hard | Date: Aug. 2 - Aug. 8 | Seed: 16 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Jenson Brooksby | Loss | 6-7 (4-7), 5-7 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 28 - Jul. 11 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Stefanos Tsitsipas | Win | 6-4, 6-4, 6-3 |
| Second Round | Vasek Pospisil | Win | 6-4, 6-4, 6-4 |
| Third Round | Karen Khachanov | Loss | 3-6, 4-6, 4-6 |
| Nature Valley International | ||
| Surface: Grass | Date: Jun. 21 - Jun. 26 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Liam Broady | Loss | 3-6, 6-7 (4-7) |
| cinch Championships | ||
| Surface: Grass | Date: Jun. 14 - Jun. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Aljaz Bedene | Win | 4-6, 6-3, 6-4 |
| Second Round | Viktor Troicki | Win | 6-3, 7-6 (7-3) |
| Quarterfinals | Denis Shapovalov | Loss | 3-6, 4-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 30 - Jun. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Steve Johnson | Loss | 7-6 (7-5), 6-3, 4-6, 2-6, 1-6 |
| Millennium Estoril Open | ||
| Surface: Red Clay | Date: Apr. 26 - May 2 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Kevin Anderson | Loss | 6-4, 6-7 (6-8), 6-7 (4-7) |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 19 - Apr. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Carlos Alcaraz | Win | 6-4, 7-6 (7-2) |
| Second Round | Diego Schwartzman | Loss | 6-3, 5-7, 1-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 23 - Apr. 4 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Stefano Travaglia | Win | 5-7, 6-4, 6-2 |
| Second Round | Daniel Evans | Win | 6-7 (5-7), 6-3, 6-3 |
| Third Round | Dusan Lajovic | Win | 1-6, 7-5, 6-3 |
| Fourth Round | Daniil Medvedev | Loss | 4-6, 3-6 |
| Abierto Mexicano Telcel presentado por HSBC | ||
| Surface: Hard | Date: Mar. 15 - Mar. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Brandon Nakashima | Win | 6-4, 6-7 (5-7), 7-6 (7-5) |
| Second Round | Lorenzo Musetti | Loss | 6-2, 3-6, 6-7 (1-7) |
| Chile Dove Men+Care Open | ||
| Surface: Red Clay | Date: Mar. 8 - Mar. 14 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Nicolas Jarry | Win | 7-6 (9-7), 6-7 (7-9), 7-6 (9-7) |
| Second Round | Facundo Bagnis | Loss | 6-7 (3-7), 6-7 (2-7) |
| Argentina Open | ||
| Surface: Clay | Date: Mar. 1 - Mar. 7 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Facundo Bagnis | Win | 6-1, 6-3 |
| Second Round | Jaume Munar | Loss | 6-7 (4-7), 4-6 |
| Australian Open | ||
| Surface: Hard | Date: Feb. 8 - Feb. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Stefano Travaglia | Win | 7-6 (7-5), 6-2, 6-2 |
| Second Round | Novak Djokovic | Loss | 3-6, 7-6 (7-3), 6-7 (2-7), 3-6 |
| Murray River Open | ||
| Surface: Hard | Date: Feb. 1 - Feb. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Corentin Moutet | Loss | 6-3, 4-6, 4-6 |
| Delray Beach Open by VITACOST.com | ||
| Surface: Hard | Date: Jan. 7 - Jan. 13 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Donald Young | Win | 6-3, 6-4 |
| Second Round | Bjorn Fratangelo | Win | 6-4, 3-6, 6-1 |
| Quarterfinals | Cameron Norrie | Loss | 0-6, 6-3, 4-6 |
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