| ||||||||||||||
| St. Petersburg Open | ||
| Surface: Hard | Date: Sep. 17 - Sep. 23 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Daniil Medvedev | Loss | 4-6, 1-6 |
| US Open | ||
| Surface: Hard | Date: Aug. 27 - Sep. 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marcel Granollers | Win | 6-2, 6-2, 6-3 |
| Second Round | Pablo Carreno Busta | Win | 4-6, 6-3, 5-7, 6-2, 2-0 Retired |
| Third Round | Lucas Pouille | Win | 7-6 (7-5), 4-6, 7-6 (7-4), 7-6(7-5) |
| Fourth Round | Novak Djokovic | Loss | 3-6, 4-6, 3-6 |
| Winston-Salem Open | ||
| Surface: Hard | Date: Aug. 19 - Aug. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Andreas Seppi | Loss | 5-7, 4-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 12 - Aug. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Peter Gojowczyk | Loss | 6-2, 4-6, 5-7 |
| Rogers Cup presented by National Bank | ||
| Surface: Hard | Date: Aug. 6 - Aug. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marton Fucsovics | Loss | 4-6, 6-7 (2-7) |
| J. Safra Sarasin Suisse Open Gstaad | ||
| Surface: Clay | Date: Jul. 23 - Jul. 29 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Facundo Bagnis | Loss | 6-4, 3-6, 5-7 |
| Plava Laguna Croatia Open Umag | ||
| Surface: Clay | Date: Jul. 16 - Jul. 22 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Aljaz Bedene | Loss | 6-7 (5-7), 6-4, 4-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 2 - Jul. 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Sergiy Stakhovsky | Loss | 3-6, 3-6, 7-5, 6-1, 4-6 |
| Antalya Open | ||
| Surface: Grass | Date: Jun. 24 - Jun. 30 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Florian Mayer | Win | 6-2, 6-2 |
| Second Round | Mirza Basic | Win | 6-7 (4-7), 6-4, 6-4 |
| Quarterfinals | Adrian Mannarino | Loss | 6-7 (3-7), 4-6 |
| Gerry Weber Open | ||
| Surface: Grass | Date: Jun. 18 - Jun. 24 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Robin Haase | Loss | 6-4, 5-7, 4-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 27 - Jun. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Guido Pella | Loss | 2-6, 3-6, 4-6 |
| Open Parc Auvergne-Rhone-Alpes Lyon | ||
| Surface: Clay | Date: May 20 - May 26 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Filip Horansky | Loss | 4-6, 6-3, 4-6 |
| Millennium Estoril Open | ||
| Surface: Red Clay | Date: Apr. 30 - May 6 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Daniil Medvedev | Win | 7-6 (7-1), 7-5 |
| Second Round | Pedro Sousa | Win | 4-6, 7-6 (7-1), 7-5 |
| Quarterfinals | Kyle Edmund | Win | 6-3, 1-6, 6-0 |
| Semifinals | Stefanos Tsitsipas | Win | 6-4, 1-6, 7-6 (7-4) |
| Final | Frances Tiafoe | Win | 6-4, 6-4 |
| Barcelona Open Banco Sabadell | ||
| Surface: Clay | Date: Apr. 23 - Apr. 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jaume Munar | Loss | 4-6, 6-3, 5-7 |
| Grand Prix Hassan II | ||
| Surface: Red Clay | Date: Apr. 9 - Apr. 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Pedro Martinez | Win | 7-5, 7-5 |
| Second Round | Mirza Basic | Win | 6-3, 3-6, 6-4 |
| Quarterfinals | Nikoloz Basilashvili | Win | 6-2, 4-6, 6-1 |
| Semifinals | Pablo Andujar | Loss | 4-6, 4-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 20 - Apr. 1 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ryan Harrison | Win | 7-6 (7-4), 7-6 (7-4) |
| Second Round | David Goffin | Win | 6-0, 6-1 |
| Third Round | Jared Donaldson | Win | 1-6, 6-3, 6-4 |
| Fourth Round | Hyeon Chung | Loss | 4-6, 3-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 7 - Mar. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Mikhail Youzhny | Win | 4-6, 6-4, 7-6 (7-4) |
| Second Round | Alexander Zverev | Win | 7-5, 5-7, 6-4 |
| Third Round | Milos Raonic | Loss | 5-7, 6-4, 2-6 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 26 - Mar. 3 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Pierre-Hugues Herbert | Loss | 6-4, 4-6, 6-7 (8-10) |
| Open 13 Marseille | ||
| Surface: Hard | Date: Feb. 19 - Feb. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Filip Krajinovic | Loss | 6-3, 4-6, 4-6 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 12 - Feb. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Andreas Seppi | Loss | 4-6, 6-1, 2-6 |
| Garanti Koza Sofia Open | ||
| Surface: Hard | Date: Feb. 5 - Feb. 11 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Dimitar Kuzmanov | Win | 7-6 (8-6), 6-1 |
| Second Round | Maximilian Marterer | Loss | 5-7, 6-7 (6-8) |
| Australian Open | ||
| Surface: Hard | Date: Jan. 15 - Jan. 28 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Dustin Brown | Win | 6-4, 6-3, 4-6, 6-7(4-7), 6-1 |
| Second Round | Marin Cilic | Loss | 1-6, 5-7, 2-6 |
| ASB Classic | ||
| Surface: Hard | Date: Jan. 1 - Jan. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Donald Young | Win | 6-7 (8-10), 6-4, 6-2 |
| Second Round | David Ferrer | Loss | 2-6, 2-6 |
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