Round: 26 Ground: Clay
| 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 |
| ATP Memphis | 2016/02/11 01:30 | Kei Nishikori v Ryan Harrison | 6-2,7-5 |
| ATP Memphis | 2016/02/09 01:30 | Ryan Harrison v Frances Tiafoe | 6-7,7-6,6-4 |
| Challenger Dallas | 2016/02/03 18:30 | Ryan Harrison v Tim Smyczek | 0-6,7-5,4-6 |
| Challenger Knoxville | 2015/11/10 19:10 | Ryan Harrison v Blaz Kavcic | 2-6,4-6 |
| Challenger Tallahassee | 2016/04/25 18:15 | Giovanni Lapentti v Dennis Novikov | 7-6,6-3 |
| Challenger Savannah | 2016/04/19 21:35 | Denis Kudla v Giovanni Lapentti | 6-7,6-1,6-2 |
| Challenger Sarasota | 2016/04/12 16:10 | Bjorn Fratangelo v Giovanni Lapentti | 6-4,6-4 |
| ATP Houston Qual | 2016/04/02 17:55 | Giovanni Lapentti v Nicolas Kicker | 5-7,6-1,4-6 |
| Challenger San Luis Potosi | 2016/03/22 17:30 | Giovanni Lapentti v Lorenzo Giustino | 4-6,3-6 |
| Challenger Morelos | 2016/02/16 22:05 | Giovanni Lapentti v Alessandro Giannessi | 7-6,5-7,6-7 |
| Challenger Santo Domingo | 2016/02/09 17:00 | Joao Souza v Giovanni Lapentti | 6-4,5-7,6-4 |
| Challenger Knoxville | 2015/11/11 18:35 | Giovanni Lapentti v Blaz Rola | 6-4,3-6,4-6 |