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| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 12 - Aug. 19 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Bye |
| Rogers Cup presented by National Bank | ||
| Surface: Hard | Date: Aug. 6 - Aug. 12 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Stefanos Tsitsipas | Loss | 3-6, 6-7 (6-8) |
| Generali Open | ||
| Surface: Clay | Date: Jul. 30 - Aug. 4 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Martin Klizan | Loss | 1-6, 6-1, 5-7 |
| German Tennis Championships | ||
| Surface: Red Clay | Date: Jul. 23 - Jul. 29 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Corentin Moutet | Win | 6-4, 6-2 |
| Second Round | John Millman | Win | 6-2, 6-2 |
| Quarterfinals | Nicolas Jarry | Loss | 6-7 (5-7), 6-7 (7-9) |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 2 - Jul. 15 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Marcos Baghdatis | Loss | 4-6, 5-7, 0-2 Retired |
| Gerry Weber Open | ||
| Surface: Grass | Date: Jun. 18 - Jun. 24 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Mikhail Youzhny | Win | 7-6 (7-5), 6-2 |
| Second Round | Yuichi Sugita | Loss | 2-6, 5-7 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 27 - Jun. 10 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Ilya Ivashka | Win | 6-2, 6-4, 6-1 |
| Second Round | Stefanos Tsitsipas | Win | 6-2, 2-6, 6-4, 6-4 |
| Third Round | Matteo Berrettini | Win | 6-3, 6-7 (5-7), 6-3, 6-2 |
| Fourth Round | Kei Nishikori | Win | 6-2, 6-0, 5-7, 6-4 |
| Quarterfinals | Alexander Zverev | Win | 6-4, 6-2, 6-1 |
| Semifinals | Marco Cecchinato | Win | 7-5, 7-6 (12-10), 6-1 |
| Final | Rafael Nadal | Loss | 4-6, 3-6, 2-6 |
| Open Parc Auvergne-Rhone-Alpes Lyon | ||
| Surface: Clay | Date: May 20 - May 26 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Roberto Carballes Baena | Win | 6-2, 6-4 |
| Quarterfinals | Guillermo Garcia-Lopez | Win | 6-7 (4-7), 7-6 (7-0), 6-4 |
| Semifinals | Dusan Lajovic | Win | 6-4, 5-7, 6-4 |
| Final | Gilles Simon | Win | 3-6, 7-6 (7-1), 6-1 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 13 - May 20 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Fabio Fognini | Loss | 4-6, 6-1, 3-6 |
| Mutua Madrid Open | ||
| Surface: Red Clay | Date: May 5 - May 13 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Federico Delbonis | Win | 4-6, 6-3, 7-5 |
| Third Round | Borna Coric | Win | 2-6, 7-6 (7-5), 6-4 |
| Quarterfinals | Rafael Nadal | Win | 7-5, 6-3 |
| Semifinals | Kevin Anderson | Win | 6-4, 6-2 |
| Final | Alexander Zverev | Loss | 4-6, 4-6 |
| Barcelona Open Banco Sabadell | ||
| Surface: Clay | Date: Apr. 23 - Apr. 29 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Jaume Munar | Win | 7-6 (10-8), 6-1 |
| Third Round | Jozef Kovalik | Win | 7-6 (7-5), 6-2 |
| Quarterfinals | Stefanos Tsitsipas | Loss | 3-6, 2-6 |
| Monte-Carlo Rolex Masters | ||
| Surface: Clay | Date: Apr. 15 - Apr. 22 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Andrey Rublev | Win | 5-7, 7-5, 7-5 |
| Third Round | Novak Djokovic | Win | 6-7 (2-7), 6-2, 6-3 |
| Quarterfinals | Rafael Nadal | Loss | 0-6, 2-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 7 - Mar. 18 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Stefanos Tsitsipas | Win | 6-2, 3-6, 6-3 |
| Third Round | Pablo Cuevas | Loss | 6-3, 4-6, 2-4 Retired |
| Abierto Mexicano TELCEL | ||
| Surface: Hard | Date: Feb. 26 - Mar. 3 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Cameron Norrie | Win | 6-3, 5-7, 7-5 |
| Second Round | Denis Shapovalov | Win | 6-2, 6-3 |
| Quarterfinals | Juan Martin Del Potro | Loss | 2-6, 6-7 (7-9) |
| Rio Open presented by Claro HDTV | ||
| Surface: Clay | Date: Feb. 19 - Feb. 25 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Dusan Lajovic | Win | 6-2, 7-5 |
| Second Round | Pablo Andujar | Win | 4-2 Retired |
| Quarterfinals | Fernando Verdasco | Loss | 4-6, 0-6 |
| Argentina Open | ||
| Surface: Clay | Date: Feb. 12 - Feb. 18 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Horacio Zeballos | Win | 6-4, 6-3 |
| Quarterfinals | Guido Pella | Win | 7-6 (9-7), 6-4 |
| Semifinals | Gael Monfils | Win | 6-2, 6-1 |
| Final | Aljaz Bedene | Win | 6-2, 6-4 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 15 - Jan. 28 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Guido Pella | Win | 6-4, 6-4, 6-4 |
| Second Round | Denis Kudla | Win | 6-7 (6-8), 3-6, 6-3, 6-2, 6-3 |
| Third Round | Adrian Mannarino | Win | 6-4, 6-2, 7-5 |
| Fourth Round | Tennys Sandgren | Loss | 2-6, 6-4, 6-7 (4-7), 7-6 (9-7), 3-6 |
| Qatar ExxonMobil Open | ||
| Surface: Hard | Date: Jan. 1 - Jan. 6 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Evgeny Donskoy | Win | 7-6 (7-3), 6-3 |
| Second Round | Aljaz Bedene | Win | 7-5, 6-4 |
| Quarterfinals | Stefanos Tsitsipas | Win | 7-5, 6-4 |
| Semifinals | Gael Monfils | Loss | Retired |
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