Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| Challenger Charlottesville | 2019/10/29 14:00 | Kevin King v Jacob Dunbar | 6-3,6-4 |
| Challenger Charlottesville | 2019/10/28 14:00 | Dennis Novikov v Jacob Dunbar | 7-5,1-6,5-7 |
| ITF M25 Fayetteville | 2019/10/25 18:00 | Jacob Dunbar v Michael Redlicki | 3-6,2-6 |
| ITF M25 Fayetteville | 2019/10/24 15:00 | Oscar Mesquida Berg v Jacob Dunbar | 3-6,3-6 |
| ITF M25 Fayetteville | 2019/10/23 20:15 | Jacob Dunbar v Vasil Kirkov | 3-6,6-2,6-1 |
| Challenger Columbus 3 | 2019/09/17 14:00 | Jacob Dunbar v Ryan Shane | 5-7,4-6 |
| Challenger Columbus 3 | 2019/09/16 15:00 | Jacob Dunbar v Aleksandar Kovacevic | 4-6,6-3,6-2 |
| ITF M25 Memphis | 2019/08/14 23:00 | Kevin King v Jacob Dunbar | 1-6,6-4,6-3 |
| Challenger Champaign | 2019/11/12 22:15 | Sebastian Korda v Benjamin Sigouin | 6-1,6-3 |
| Challenger Champaign | 2019/11/11 19:50 | Michail Pervolarakis v Benjamin Sigouin | 6-3,3-6,2-6 |
| ITF M25 Fayetteville | 2019/10/24 17:50 | Nicolas Mejia v Benjamin Sigouin | 6-3,3-6,6-3 |
| ITF M25 Fayetteville | 2019/10/23 17:35 | Benjamin Sigouin v Tauheed Browning | 6-1,6-0 |
| ITF M25 Claremont | 2019/10/10 18:00 | Benjamin Sigouin v Hendrik Jebens | 5-7,7-5,6-4 |
| ITF M25 Claremont | 2019/10/09 18:45 | Benjamin Sigouin v Alessandro-D Ventre | 6-4,6-0 |
| Challenger Columbus 3 | 2019/09/19 15:00 | Thai-Son Kwiatkowski v Benjamin Sigouin | 6-2,6-4 |
| Challenger Columbus 3 | 2019/09/18 14:00 | Benjamin Sigouin v Renzo Olivo | 6-1,6-2 |