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