Stadium: Court 1 Round: 28 Ground: Hardcourt indoor
| Challenger Knoxville | 2016/11/11 17:40 | Jared Donaldson v Ruben Bemelmans | 6-3,5-7,6-4 |
| Challenger Champaign | 2016/11/17 18:00 | Jared Donaldson v Bradley Klahn | 6-4,6-4 |
| 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 Champaign | 2016/11/16 16:00 | Mitchell Krueger v Ruben Bemelmans | 6-7,2-6 |
| Challenger Champaign | 2016/11/15 21:50 | Cameron Norrie v Ruben Bemelmans | 4-6,3-6 |
| Challenger Knoxville | 2016/11/11 17:40 | Jared Donaldson v Ruben Bemelmans | 6-3,5-7,6-4 |
| Challenger Knoxville | 2016/11/10 15:00 | Ruben Bemelmans v Noah Rubin | 6-4,6-4 |
| Challenger Knoxville | 2016/11/09 16:40 | Ruben Bemelmans v Joris De Loore | 5-7,7-6,6-4 |
| Challenger Charlottesville | 2016/11/06 19:20 | Reilly Opelka v Ruben Bemelmans | 6-4,2-6,7-6 |
| Challenger Charlottesville | 2016/11/05 19:40 | Ruben Bemelmans v Henri Laaksonen | 4-6,6-4,7-6 |
| Challenger Charlottesville | 2016/11/04 23:05 | Tim Smyczek v Ruben Bemelmans | 2-6,4-6 |