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