Round: 26 Ground: Grass
| 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 |
| Challenger Wroclaw | 2016/02/17 15:55 | Marco Chiudinelli v Mirza Basic | 7-6,7-6 |
| ATP Newport | 2016/07/12 15:00 | John-Patrick Smith v Jordan Thompson | 6-4,6-4 |
| Wimbledon Qual | 2016/06/21 11:35 | John-Patrick Smith v Austin Krajicek | 2-6,6-3,9-11 |
| Challenger Le Gosier | 2016/04/05 23:20 | John-Patrick Smith v Thiago Monteiro | 7-6,5-7,6-7 |
| ATP Miami Qual | 2016/03/21 17:15 | Mischa Zverev v John-Patrick Smith | 6-4,6-4 |
| ATP Delray Beach | 2016/02/19 01:00 | John-Patrick Smith v Juan Martin Del Potro | 4-6,4-6 |
| ATP Delray Beach | 2016/02/16 01:00 | Ivo Karlovic v John-Patrick Smith | 3-6,6-3,2-6 |
| ATP Delray Beach Qual | 2016/02/14 16:00 | Alejandro Falla v John-Patrick Smith | 2-6,6-2,1-6 |
| ATP Delray Beach Qual | 2016/02/13 16:00 | Andrey Rublev v John-Patrick Smith | 6-4,3-6,0-6 |