Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| Challenger Champaign | 2019/11/15 00:00 | JC Aragone v Alexander Brown | 6-7,3-6 |
| Challenger Champaign | 2019/11/13 02:10 | JC Aragone v Jelle Sels | 6-2,3-6,6-3 |
| Challenger Knoxville | 2019/11/04 16:30 | JC Aragone v Ernesto Escobedo | 6-7,6-7 |
| Challenger Charlottesville | 2019/10/31 00:40 | Denis Kudla v JC Aragone | 6-4,6-4 |
| Challenger Charlottesville | 2019/10/29 18:20 | JC Aragone v Roberto Cid Subervi | 6-2,6-3 |
| Challenger Las Vegas | 2019/10/14 22:45 | JC Aragone v Laurent Lokoli | 7-6,7-5 |
| Challenger Fairfield | 2019/10/08 18:50 | JC Aragone v Maxime Cressy | 6-7,2-6 |
| Challenger Fairfield | 2019/10/07 19:15 | Roy Smith v JC Aragone | 6-7,4-6 |
| Challenger Ann Arbor | 2020/01/06 20:00 | Ondrej Styler v Andrew Fenty | 6-7,6-7 |
| ITF M25 Memphis | 2019/08/12 21:20 | Andrew Fenty v Abraham Asaba | 6-3,2-6,9-11 |
| ITF M25 Edwardsville | 2019/08/06 14:00 | Carson Haskins v Andrew Fenty | 4-6,6-1,10-5 |
| ATP Washington | 2019/07/27 16:15 | Viktor Troicki v Andrew Fenty | 4-6,6-1,7-5 |
| Challenger Binghamton | 2019/07/23 21:35 | Sekou Bangoura v Andrew Fenty | 6-3,7-5 |
| ITF M25 Iowa City | 2019/07/16 17:20 | Preston Touliatos v Andrew Fenty | 6-4,6-1 |
| ITF M25 Iowa City | 2019/07/15 15:00 | Elio Jose Ribeiro Lago v Andrew Fenty | 3-6,1-6 |
| ITF M15 Norman | 2019/07/12 15:00 | Andrew Fenty v Mark Whitehouse | 4-6,2-6 |