Stadium: Court 4 Round: 25 Ground: Hardcourt outdoor
| ATP Delray Beach | 2019/02/17 16:00 | Adrian Menendez-Maceiras v Tim Smyczek | 3-6,4-6 |
| ATP Delray Beach | 2019/02/16 17:05 | Tim Smyczek v Yasutaka Uchiyama | 6-4,6-2 |
| ATP New York | 2019/02/11 18:00 | Ramkumar Ramanathan v Tim Smyczek | 6-3,3-6,7-5 |
| ATP New York | 2019/02/10 19:45 | Tim Smyczek v Roberto Quiroz | 6-7,6-3,7-5 |
| Challenger Dallas | 2019/02/06 20:45 | Marcos Giron v Tim Smyczek | 6-7,6-2,7-6 |
| Challenger Cleveland | 2019/01/31 16:20 | Maxime Cressy v Tim Smyczek | 6-4,6-3 |
| Challenger Cleveland | 2019/01/30 15:00 | Liam Broady v Tim Smyczek | 4-6,3-6 |
| Australian Open | 2019/01/11 00:45 | Tim Smyczek v Gleb Sakharov | 6-3,3-6,4-6 |
| ATP New York | 2019/02/15 17:00 | Paolo Lorenzi v Brayden Schnur | 7-6,6-7,5-7 |
| ATP New York | 2019/02/13 17:55 | Paolo Lorenzi v Ryan Harrison | 4-6,6-4,6-4 |
| ATP New York | 2019/02/11 19:55 | Tennys Sandgren v Paolo Lorenzi | 6-7,7-6,4-6 |
| ATP Córdoba | 2019/02/04 22:10 | Paolo Lorenzi v Guido Pella | 1-6,3-6 |
| ATP Córdoba | 2019/02/03 20:25 | Paolo Lorenzi v Alessandro Giannessi | 7-6,4-6,6-7 |
| ATP Córdoba | 2019/02/02 22:05 | Paolo Lorenzi v Facundo Arguello | 3-6,6-3,6-4 |
| Challenger Newport Beach | 2019/01/22 19:40 | Paolo Lorenzi v Filip Peliwo | 4-6,6-3,4-6 |
| Australian Open | 2019/01/11 00:50 | Paolo Lorenzi v Daniel Evans | 3-6,3-6 |