Stadium: EVE ZIMMERMAN COURT Round: 25 Ground: Hardcourt outdoor
| Challenger Santiago 2 Qual | 2016/03/10 21:00 | Alessandro Giannessi v Gonzalo Lama | 7-5,2-6,6-7 |
| Challenger Santiago 2 Qual | 2016/03/08 19:45 | Alessandro Giannessi v Christian Lindell | 7-6,7-5 |
| Challenger Morelos | 2016/02/19 17:00 | Alessandro Giannessi v Alejandro Gonzalez | 3-6,1-6 |
| Challenger Morelos | 2016/02/18 19:30 | Alessandro Giannessi v Alexander Sarkissian | 2-6,6-1,6-3 |
| Challenger Morelos | 2016/02/17 20:35 | Alessandro Giannessi v Guido Andreozzi | 1-6,6-4,7-5 |
| Challenger Morelos | 2016/02/16 22:05 | Giovanni Lapentti v Alessandro Giannessi | 7-6,5-7,6-7 |
| Challenger Santo Domingo | 2016/02/12 20:30 | Nicolas Kicker v Alessandro Giannessi | 6-4,3-6,6-2 |
| Challenger Santo Domingo | 2016/02/10 18:00 | Franko Skugor v Alessandro Giannessi | 6-7,6-7 |
| Challenger Heilbronn Qual | 2016/05/07 09:50 | James McGee v Edoardo Eremin | 6-4,3-6,0-6 |
| Challenger Tallahassee | 2016/04/29 18:00 | Quentin Halys v James McGee | 6-4,6-1 |
| Challenger Tallahassee | 2016/04/28 15:00 | James McGee v Stefan Kozlov | 6-3,2-6,7-6 |
| Challenger Tallahassee | 2016/04/27 18:45 | Nikoloz Basilashvili v James McGee | 3-6,0-6 |
| Challenger Tallahassee | 2016/04/26 15:50 | Nicolas Jarry v James McGee | 7-5,5-7,3-6 |
| Challenger Tallahassee Qual | 2016/04/24 14:00 | James McGee v Marc Polmans | 6-3,6-3 |
| Challenger Tallahassee Qual | 2016/04/23 16:55 | James McGee v Rubin Statham | 6-4,6-3 |
| Challenger Savannah | 2016/04/19 15:00 | James McGee v Tomas Lipovsek Puches | 5-7,3-6 |