Round: 27 Ground: Grass
| Newport, USA | 2016/07/13 16:30 | Chiudinelli, Marco v Smith, John-Patrick | 1-6,6-3,6-3 |
| Wimbledon Qual | 2016/06/21 11:10 | Kudryavtsev, Alexander v Chiudinelli, Marco | 7-5,3-6,6-3 |
| French Open Qual | 2016/05/16 11:10 | Chiudinelli, Marco v Laslo Djere | 4-6,0-6 |
| ATP Geneva Qual | 2016/05/14 10:55 | Chiudinelli, Marco v Yann Marti | 3-6,2-6 |
| Coupe Davis | 2016/03/04 13:00 | Lorenzi, Paolo v Chiudinelli, Marco | 7-6,6-3,4-6,5-7,7-5 |
| Challenger Wroclaw | 2016/02/21 15:00 | Chiudinelli, Marco v Hernych, Jan | 6-3,7-6 |
| Challenger Wroclaw | 2016/02/20 13:30 | Kravchuk, Konstantin v Chiudinelli, Marco | 6-7,6-7 |
| Challenger Wroclaw | 2016/02/19 13:30 | Kudryavtsev, Alexander v Chiudinelli, Marco | 3-6,2-6 |
| Newport, USA | 2016/07/13 15:00 | Dancevic, Frank v Karlovic, Ivo | 6-3,6-7,4-6 |
| Wimbledon, London, Great Britain | 2016/06/30 11:00 | Lacko, Lukas v Karlovic, Ivo | 6-3,3-6,7-6,6-4 |
| Wimbledon, London, Great Britain | 2016/06/27 10:30 | Borna Coric v Karlovic, Ivo | 6-7,6-7,4-6 |
| ATP Halle | 2016/06/16 10:00 | Kohlschreiber, Philipp v Karlovic, Ivo | 6-7,6-4,7-5 |
| ATP Halle | 2016/06/14 13:15 | Karlovic, Ivo v Andrey Kuznetsov | 7-6,6-3 |
| Open de France | 2016/05/27 11:05 | Karlovic, Ivo v Andy Murray | 1-6,4-6,6-7 |
| Open de France | 2016/05/25 09:00 | Karlovic, Ivo v Jordan Thompson | 6-7,6-3,7-6,6-7,12-10 |
| Open de France | 2016/05/23 13:30 | Karlovic, Ivo v Montanes, Albert | 6-2,7-6,7-6 |