Stadium: Court 1 Round: 26 Ground: Hardcourt indoor
| Challenger Champaign | 2016/11/16 01:25 | Jared Donaldson v Daniel Cox | 6-4,6-3 |
| Challenger Knoxville | 2016/11/12 15:00 | Peter Polansky v Jared Donaldson | 6-2,6-4 |
| Challenger Knoxville | 2016/11/11 17:40 | Jared Donaldson v Ruben Bemelmans | 6-3,5-7,6-4 |
| Challenger Knoxville | 2016/11/11 00:10 | Jared Donaldson v Rhyne Williams | 6-4,7-5 |
| Challenger Knoxville | 2016/11/08 22:30 | Jared Donaldson v Mikelis Libietis | 6-2,6-4 |
| Challenger Charlottesville | 2016/11/04 17:25 | Henri Laaksonen v Jared Donaldson | 6-3,7-5 |
| Challenger Charlottesville | 2016/11/02 18:00 | Liam Broady v Jared Donaldson | 4-6,6-7 |
| Challenger Charlottesville | 2016/10/31 23:35 | Alexander Ritschard v Jared Donaldson | 2-6,6-3,3-6 |
| Challenger Champaign | 2016/11/16 00:00 | Noe Khlif v Ryan Shane | 2-6,4-6 |
| Challenger Champaign Qual | 2016/11/14 16:00 | Dragos Constantin Ignat v Ryan Shane | 0-6,3-6 |
| Challenger Champaign Qual | 2016/11/13 17:15 | Kevin King v Ryan Shane | 4-6,1-6 |
| Challenger Knoxville Qual | 2016/11/07 15:00 | Ryan Shane v Peter Kobelt | 6-7,7-5,3-6 |
| Challenger Knoxville Qual | 2016/11/06 15:00 | Ryan Shane v Jonathan Ho | 6-2,6-2 |
| Challenger Charlottesville | 2016/11/01 22:40 | Frances Tiafoe v Ryan Shane | 6-3,2-6,6-4 |
| Challenger Cary | 2016/09/15 17:00 | Ernesto Escobedo v Ryan Shane | 6-3,5-7,6-1 |
| Challenger Cary | 2016/09/13 18:05 | Adam El Mihdawy v Ryan Shane | 2-6,6-7 |