Stadium: Court 3 Round: 27 Ground: Hardcourt indoor
| Challenger Columbus | 2018/09/15 18:25 | Dunbar, Jacob v Cannon Kingsley | 2-6,7-6,2-6 |
| ITF M15 East Lansing | 2019/11/20 21:15 | Cannon Kingsley v Siimar, Mattias | 7-5,6-2 |
| Challenger Charlottesville | 2019/10/28 14:00 | Caruana, Liam v Cannon Kingsley | 6-3,7-6 |
| Columbus III, USA | 2019/09/17 17:45 | Thai-Son Kwiatkowski v Cannon Kingsley | 3-6,6-4,6-3 |
| Columbus III, USA | 2019/09/16 20:10 | Song, Evan v Cannon Kingsley | 4-6,6-2,2-6 |
| ITF M25 Champaign | 2019/07/26 21:00 | Cannon Kingsley v Aleksandar Kovacevic | 4-6,4-6 |
| ITF M25 Champaign | 2019/07/25 17:00 | Cannon Kingsley v Shabaz, Michael | 6-7,6-2,6-4 |
| ITF M25 Champaign | 2019/07/23 18:35 | Cannon Kingsley v Bushamuka, William | 6-3,6-4 |
| Challenger Columbus | 2019/06/10 22:45 | Cannon Kingsley v Nam, Ji Sung | 5-7,4-6 |
| ITF M15 East Lansing | 2019/11/21 18:25 | Hinsching, Joao v Dunbar, Jacob | 1-6,3-6 |
| ITF M15 East Lansing | 2019/11/20 20:40 | Dunbar, Jacob v Sigouin, Benjamin | 7-5,6-1 |
| Challenger Charlottesville | 2019/10/29 14:00 | King, Kevin v Dunbar, Jacob | 6-3,6-4 |
| Challenger Charlottesville | 2019/10/28 14:00 | Novikov, Dennis v Dunbar, Jacob | 7-5,1-6,5-7 |
| Fayetteville, AR, Singles Qualifying, M-ITF-USA-31 | 2019/10/25 18:00 | Dunbar, Jacob v Redlicki, Michael | 3-6,2-6 |
| Fayetteville, AR, Singles Qualifying, M-ITF-USA-31 | 2019/10/24 15:00 | Mesquida Berg, Oscar v Dunbar, Jacob | 3-6,3-6 |
| Fayetteville, AR, Singles Qualifying, M-ITF-USA-31 | 2019/10/23 20:15 | Dunbar, Jacob v Kirkov, Vasil | 3-6,6-2,6-1 |
| Columbus III, USA | 2019/09/17 14:00 | Dunbar, Jacob v Shane, Ryan | 5-7,4-6 |