Stadium: Court 5 Round: 24 Ground: Hardcourt outdoor
| Challenger Aptos MD | 2019/08/07 23:30 | Cerretani/Erlich v Cressy/Smith | 6-3,6-1 |
| Challenger Lexington MD | 2019/08/02 00:30 | Maytin/Withrow v Cressy/Smith | 6-7,6-4,10-6 |
| Challenger Lexington MD | 2019/07/31 23:00 | Cressy/Smith v Gabashvili/Uzhylovskyi | 6-3,6-2 |
| ATP Newport MD | 2019/07/15 18:15 | Monroe/Zverev v Cressy/Smith | 7-6,6-7,10-7 |