Stadium: Court 3 Round: 25 Ground: Hardcourt indoor
| Challenger Fairfield | 2019/10/08 17:00 | Kevin King v Altug Celikbilek | 6-4,6-3 |
| ITF M25 Norman | 2019/10/05 17:45 | Kevin King v Hugo Gaston | 3-6,3-6 |
| ITF M25 Norman | 2019/10/04 15:00 | Evan Zhu v Kevin King | 3-6,2-6 |
| ITF M25 Norman | 2019/10/03 18:00 | Alexander Cozbinov v Kevin King | 1-6,0-6 |
| ITF M25 Norman | 2019/10/02 17:35 | Adrian Andreev v Kevin King | 3-6,5-7 |
| Challenger Cary | 2019/09/10 20:50 | Kevin King v Enzo Couacaud | 1-6,2-6 |
| Challenger Cary | 2019/09/09 23:15 | Strong Kirchheimer v Kevin King | 4-6,6-2,2-6 |
| ATP Winston-Salem | 2019/08/17 17:35 | Damir Dzumhur v Kevin King | 6-4,2-6,6-1 |
| Challenger Fairfield | 2019/10/08 19:55 | Roberto Quiroz v Christopher O'Connell | 3-6,4-6 |
| Challenger Sibiu | 2019/09/22 13:50 | Christopher O'Connell v Danilo Petrovic | 4-6,2-6 |
| Challenger Sibiu | 2019/09/21 12:00 | Christopher O'Connell v Jelle Sels | 4-6,6-4,6-2 |
| Challenger Sibiu | 2019/09/20 09:20 | Christopher O'Connell v Vit Kopriva | 7-5,6-3 |
| Challenger Sibiu | 2019/09/19 10:20 | Pedro Sousa v Christopher O'Connell | 4-6,1-6 |
| Challenger Sibiu | 2019/09/17 10:50 | Maxime Hamou v Christopher O'Connell | 7-6,6-7,2-6 |
| Challenger Banja Luka | 2019/09/10 13:35 | Matija Pecotic v Christopher O'Connell | 6-3,5-7,7-6 |
| Challenger Como | 2019/08/29 12:15 | Christopher O'Connell v Andrej Martin | 2-6,2-6 |