| 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 | 2016/05/10 09:00 | Ryan Harrison v Renzo Olivo | 6-3,3-6,2-6 |
| Challenger Tallahassee | 2016/04/29 23:35 | Frances Tiafoe v Ryan Harrison | 7-6,6-4 |
| Challenger Tallahassee | 2016/04/28 19:30 | Noah Rubin v Ryan Harrison | 6-2,0-6,3-6 |
| Challenger Tallahassee | 2016/04/27 19:45 | Ryan Harrison v Giovanni Lapentti | 6-3,6-4 |
| Challenger Tallahassee | 2016/04/26 19:15 | Henri Laaksonen v Ryan Harrison | 3-6,6-7 |
| Challenger Savannah | 2016/04/18 21:30 | Jared Donaldson v Ryan Harrison | 6-2,7-6 |
| Challenger Sarasota | 2016/04/11 19:35 | Guilherme Clezar v Ryan Harrison | 7-5,6-2 |
| ATP Miami Qual | 2016/03/21 18:50 | Horacio Zeballos v Ryan Harrison | 6-7,6-3,6-4 |