| ||||||||||||||
| US Open | ||
| Surface: Hard | Date: Aug. 29 - Sep. 11 | Seed: 25 |
| Round | Opponent | W / L | Result |
| First Round | Nicolas Mahut | Loss | 3-6, 5-7, 0-1 Retired |
| Generali Open | ||
| Surface: Clay | Date: Jul. 18 - Jul. 24 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Karen Khachanov | Loss | 4-6, 4-6 |
| German Tennis Championships 2016 | ||
| Surface: Red Clay | Date: Jul. 11 - Jul. 17 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Carlos Berlocq | Win | 6-3, 6-7 (5-7), 6-3 |
| Second Round | Nicolas Kicker | Win | 4-6, 6-1, 6-2 |
| Quarterfinals | Renzo Olivo | Loss | 6-1, 0-6, 5-7 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 27 - Jul. 10 | Seed: 21 |
| Round | Opponent | W / L | Result |
| First Round | Pierre-Hugues Herbert | Loss | 5-7, 3-6, 6-3, 3-6 |
| Gerry Weber Open | ||
| Surface: Grass | Date: Jun. 13 - Jun. 19 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Marcel Granollers | Win | 6-2, 7-6 (7-4) |
| Second Round | Ivo Karlovic | Win | 6-7 (7-9), 6-4, 7-5 |
| Quarterfinals | Dominic Thiem | Loss | Retired |
| MercedesCup | ||
| Surface: Grass | Date: Jun. 6 - Jun. 13 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Pierre-Hugues Herbert | Win | 6-4, 6-1 |
| Second Round | Denis Kudla | Win | 7-5, 6-3 |
| Quarterfinals | Radek Stepanek | Win | 6-4, 7-5 |
| Semifinals | Juan Martin del Potro | Win | 6-3, 6-4 |
| Final | Dominic Thiem | Loss | 7-6 (7-2), 4-6, 4-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 22 - Jun. 5 | Seed: 24 |
| Round | Opponent | W / L | Result |
| First Round | Nicolas Almagro | Loss | 7-5, 2-6, 2-6, 4-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 8 - May 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Inigo Cervantes | Win | 6-4, 6-2 |
| Second Round | Rafael Nadal | Loss | 3-6, 3-6 |
| Mutua Madrid Open | ||
| Surface: Red Clay | Date: Apr. 30 - May 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Pablo Cuevas | Loss | 3-6, 6-3, 6-7 (5-7) |
| BMW Open by FWU AG | ||
| Surface: Red Clay | Date: Apr. 25 - May 1 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Florian Mayer | Win | 6-3, 6-2 |
| Quarterfinals | Juan Martin del Potro | Win | 6-4, 6-1 |
| Semifinals | Fabio Fognini | Win | 6-1, 6-4 |
| Final | Dominic Thiem | Win | 7-6 (9-7), 4-6, 7-6 (7-4) |
| Barcelona Open BancSabadell | ||
| Surface: Clay | Date: Apr. 18 - Apr. 24 | Seed: 10 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Pablo Carreno Busta | Win | 6-2, 6-1 |
| Third Round | Feliciano Lopez | Win | 6-7 (5-7), 7-5, 6-3 |
| Quarterfinals | Andrey Kuznetsov | Win | 6-3, 6-1 |
| Semifinals | Rafael Nadal | Loss | 3-6, 3-6 |
| Monte-Carlo Rolex Masters | ||
| Surface: Clay | Date: Apr. 10 - Apr. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Borna Coric | Win | 6-4, 6-4 |
| Second Round | Stan Wawrinka | Loss | 6-7 (2-7), 5-7 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 9 - Mar. 20 | Seed: 27 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Denis Kudla | Win | 6-0, 6-1 |
| Third Round | Novak Djokovic | Loss | 5-7, 5-7 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 22 - Feb. 28 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Marsel Ilhan | Win | 6-1, 7-5 |
| Second Round | Borna Coric | Win | 6-2, 7-6 (7-5) |
| Quarterfinals | Stan Wawrinka | Loss | 5-7, 1-6 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 8 - Feb. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Julien Benneteau | Win | 6-4, 6-4 |
| Second Round | Ivan Dodig | Win | 6-4, 6-2 |
| Quarterfinals | Marin Cilic | Win | 3-6, 6-3, 6-4 |
| Semifinals | Gael Monfils | Loss | 3-6, 2-6 |
| Garanti Koza Sofia Open | ||
| Surface: Hard | Date: Feb. 1 - Feb. 7 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Sergiy Stakhovsky | Win | 6-2, 6-2 |
| Second Round | Damir Dzumhur | Win | 6-1, 4-6, 6-3 |
| Quarterfinals | Viktor Troicki | Loss | 3-6, 4-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 17 - Jan. 31 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Kei Nishikori | Loss | 4-6, 3-6, 3-6 |
| ASB Classic | ||
| Surface: Hard | Date: Jan. 4 - Jan. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Benjamin Becker | Win | 7-6 (10-8), 6-3 |
| Second Round | Jo-Wilfried Tsonga | Loss | 3-6, 4-6 |
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