Stadium: COURT 4 Round: 46 Ground: Hardcourt outdoor
| ATP Houston | 2014/04/08 18:40 | Ryan Harrison v Donald Young | 0-6,1-6 |
| Challenger Tallahassee | 2016/04/28 23:55 | Donald Young v Frances Tiafoe | 6-2,4-6,3-6 |
| Challenger Tallahassee | 2016/04/27 16:25 | Donald Young v Daniil Medvedev | 6-4,7-6 |
| Challenger Tallahassee | 2016/04/26 21:20 | Donald Young v Ernesto Escobedo | 6-3,6-4 |
| Challenger Savannah | 2016/04/23 19:25 | Jared Donaldson v Donald Young | 6-4,6-3 |
| Challenger Savannah | 2016/04/22 19:10 | Nicolas Kicker v Donald Young | 4-6,5-7 |
| Challenger Savannah | 2016/04/18 23:25 | Noah Rubin v Donald Young | 5-7,6-7 |
| ATP Houston | 2016/04/07 18:00 | Donald Young v Tim Smyczek | 2-6,4-6 |
| ATP Houston | 2016/04/05 18:20 | Steve Johnson v Donald Young | 4-6,3-6 |
| 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 |