Round: 27 Ground: Hardcourt indoor
| Challenger Champaign | 2016/11/16 20:05 | Jared Donaldson v Ryan Shane | 6-2,6-4 |
| 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 Champaign | 2016/11/16 16:00 | Tennys Sandgren v Bradley Klahn | 6-4,3-6,4-6 |
| Challenger Champaign Qual | 2016/11/14 16:00 | Bradley Klahn v Ruan Roelofse | 6-3,6-2 |
| Challenger Champaign Qual | 2016/11/13 17:30 | Peter Kobelt v Bradley Klahn | 6-4,0-6,6-7 |
| Challenger Champaign Qual | 2016/11/12 16:00 | Bradley Klahn v Tim Kopinski | 6-2,6-1 |
| Challenger Launceston | 2015/02/13 00:00 | Bjorn Fratangelo v Bradley Klahn | 7-6,6-3 |
| Challenger Launceston | 2015/02/12 00:00 | Dayne Kelly v Bradley Klahn | 7-5,3-6,2-6 |
| Challenger Launceston | 2015/02/10 06:00 | Matthew Ebden v Bradley Klahn | 0-6,4-6 |
| Challenger Traralgon | 2014/11/04 00:55 | Benjamin Mitchell v Bradley Klahn | 6-4,2-6,6-4 |