Round: 27 Ground: Clay
| Challenger Tallahassee | 2016/04/27 23:35 | Brian Baker v Noah Rubin | 5-7,7-6,2-6 |
| Challenger Tallahassee | 2016/04/25 16:05 | Eric Quigley v Noah Rubin | 4-6,7-5,3-6 |
| Challenger Savannah | 2016/04/18 23:25 | Noah Rubin v Donald Young | 5-7,6-7 |
| Challenger Sarasota | 2016/04/15 21:00 | Noah Rubin v Guilherme Clezar | 3-6,0-6 |
| Challenger Sarasota | 2016/04/13 16:15 | Noah Rubin v Gonzalo Lama | 6-0,7-6 |
| Challenger Sarasota | 2016/04/11 21:10 | Denis Kudla v Noah Rubin | 5-7,6-2,6-7 |
| ATP Miami Qual | 2016/03/22 17:20 | Tatsuma Ito v Noah Rubin | 6-4,6-4 |
| ATP Miami Qual | 2016/03/21 19:15 | Noah Rubin v Mirza Basic | 6-2,6-2 |
| 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 |
| 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 |