Stadium: Court 2 Round: 24 Ground: Hardcourt outdoor
| Challenger Aptos | 2019/08/05 19:55 | Maxime Janvier v Duckhee Lee | 6-4,4-6,6-4 |
| Challenger Lexington | 2019/08/02 23:40 | Jannik Sinner v Duckhee Lee | 4-6,6-3,6-1 |
| Challenger Lexington | 2019/08/01 14:00 | Evgeny Karlovskiy v Duckhee Lee | 6-4,2-6,4-6 |
| Challenger Lexington | 2019/07/30 16:25 | Nicolas Moreno De Alboran v Duckhee Lee | 2-6,3-6 |
| Challenger Binghamton | 2019/07/26 15:00 | Duckhee Lee v Joao Menezes | 5-7,2-6 |
| Challenger Binghamton | 2019/07/25 17:35 | Teymuraz Gabashvili v Duckhee Lee | 4-6,3-6 |
| Challenger Binghamton | 2019/07/24 21:00 | Aleksandar Vukic v Duckhee Lee | 3-6,3-6 |
| Challenger Gatineau | 2019/07/19 20:00 | Duckhee Lee v Jason Kubler | 2-6,3-6 |
| Challenger Lexington | 2019/08/01 17:55 | Alexander Ritschard v Maverick Banes | 6-4,6-2 |
| Challenger Lexington | 2019/07/31 18:45 | John McNally v Maverick Banes | 6-7,6-3,1-6 |
| Challenger Granby | 2019/07/24 15:10 | Maverick Banes v Alexis Galarneau | 3-6,2-6 |
| Challenger Gatineau | 2019/07/15 20:05 | Maverick Banes v Cem Ilkel | 3-6,2-6 |
| Challenger Milan | 2019/06/26 11:00 | Maverick Banes v Marcelo Arevalo | 1-6,4-6 |
| Challenger Parma | 2019/06/20 10:45 | Martin Cuevas v Maverick Banes | 6-4,6-0 |
| Challenger Parma | 2019/06/19 10:55 | Andrea Basso v Maverick Banes | 1-6,6-7 |
| ATP Stuttgart | 2019/06/08 11:20 | Maverick Banes v Alexei Popyrin | 6-4,3-6,6-7 |