Round: 26 Ground: Clay
| Challenger Cali 2 | 2016/07/05 23:00 | Darian King v Alejandro Gomez | 6-4,6-0 |
| ITF USA F23 | 2016/06/28 15:45 | Darian King v Felix Corwin | 3-6,6-2,4-6 |
| Wimbledon Qual | 2016/06/22 13:30 | Adam Pavlasek v Darian King | 6-3,6-4 |
| Wimbledon Qual | 2016/06/21 11:35 | Darian King v Ti Chen | 1-6,6-4,10-8 |
| ITF USA F18 | 2016/06/19 14:00 | Sekou Bangoura v Darian King | 6-3,6-2 |
| ITF USA F18 | 2016/06/18 15:00 | Peter Polansky v Darian King | 7-5,2-6,0-6 |
| ITF USA F18 | 2016/06/17 14:30 | Eric Quigley v Darian King | 6-7,1-6 |
| ITF USA F18 | 2016/06/15 18:50 | Gonzales Austin v Darian King | 6-7,1-6 |
| Challenger Cali 2 | 2016/07/05 17:55 | Giovanni Lapentti v Christopher Diaz-Figueroa | 7-5,7-6 |
| Challenger Marburg | 2016/06/28 12:15 | Steve Darcis v Giovanni Lapentti | 6-2,7-6 |
| Challenger Marburg Qual | 2016/06/27 11:00 | Germain Gigounon v Giovanni Lapentti | 6-4,6-0 |
| Challenger Marburg Qual | 2016/06/26 13:30 | Maxime Tabatruong v Giovanni Lapentti | 5-7,3-6 |
| Challenger Marburg Qual | 2016/06/26 08:00 | Matej Sabanov v Giovanni Lapentti | 6-3,5-7,5-7 |
| ATP Stuttgart Qual | 2016/06/04 12:40 | Yuichi Sugita v Giovanni Lapentti | 6-3,6-1 |
| ITF Romania F4 | 2016/05/24 08:30 | Giovanni Lapentti v Juan Pablo Paz | 3-6,6-4,5-7 |
| Challenger Bordeaux Qual | 2016/05/08 10:20 | Giovanni Lapentti v Tommy Paul | 1-6,1-6 |