Stadium: Court 3 Round: 27 Ground: Hardcourt indoor
| Challenger Columbus | 2018/09/15 18:25 | Jacob Dunbar v Cannon Kingsley | 2-6,7-6,2-6 |
| ITF - East Lansing M15 | 2019/11/20 21:15 | Cannon Kingsley v Mattias Siimar | 7-5,6-2 |
| Challenger Charlottesville | 2019/10/28 14:00 | Liam Caruana v Cannon Kingsley | 6-3,7-6 |
| Challenger Columbus 3 | 2019/09/17 17:45 | Thai-Son Kwiatkowski v Cannon Kingsley | 3-6,6-4,6-3 |
| Challenger Columbus 3 | 2019/09/16 20:10 | Evan Song v Cannon Kingsley | 4-6,6-2,2-6 |
| ITF - Champaign M25 | 2019/07/26 21:00 | Cannon Kingsley v Aleksandar Kovacevic | 4-6,4-6 |
| ITF - Champaign M25 | 2019/07/25 17:00 | Cannon Kingsley v Michael Shabaz | 6-7,6-2,6-4 |
| ITF - Champaign M25 | 2019/07/23 18:35 | Cannon Kingsley v William Bushamuka | 6-3,6-4 |
| Challenger Columbus | 2019/06/10 22:45 | Cannon Kingsley v Ji Sung Nam | 5-7,4-6 |
| ITF - East Lansing M15 | 2019/11/21 18:25 | Joao Hinsching v Jacob Dunbar | 1-6,3-6 |
| ITF - East Lansing M15 | 2019/11/20 20:40 | Jacob Dunbar v Benjamin Sigouin | 7-5,6-1 |
| 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 |