Stadium: Center Court Round: 27 Ground: Hardcourt outdoor
| French Open | 2019/05/21 08:00 | Mathias Bourgue v Matteo Viola | 4-6,6-1,6-3 |
| Challenger Heilbronn | 2019/05/14 11:20 | Matteo Viola v Attila Balazs | 4-6,3-6 |
| Challenger Rome | 2019/05/09 08:00 | Matteo Viola v Henri Laaksonen | 4-6,3-6 |
| Challenger Rome | 2019/05/07 08:00 | Matteo Viola v Renzo Olivo | 6-3,7-5 |
| Challenger Ostrava | 2019/05/01 11:40 | Matteo Viola v Ivan Gakhov | 4-6,4-6 |
| Challenger Francavilla | 2019/04/23 12:00 | Matteo Viola v Mikael Ymer | 1-6,2-6 |
| Challenger Francavilla | 2019/04/22 11:20 | Matteo Viola v Carlos Boluda-Purkiss | 6-3,6-2 |
| Challenger Anning | 2019/04/17 06:00 | Matteo Viola v Jay Clarke | 4-6,3-6 |
| Challenger Savannah | 2019/05/02 21:30 | Sumit Nagal v Sebastian Korda | 6-3,7-6 |
| Challenger Savannah | 2019/04/30 19:55 | Sebastian Korda v Mikael Torpegaard | 6-3,6-3 |
| Challenger Savannah | 2019/04/29 21:40 | Jared Hiltzik v Sebastian Korda | 4-6,0-6 |
| Challenger Tallahassee | 2019/04/23 18:30 | Sebastian Korda v Marc Polmans | 6-7,7-6,4-6 |
| Challenger Tallahassee | 2019/04/22 19:40 | Miljan Zekic v Sebastian Korda | 4-6,2-6 |
| Challenger Sarasota | 2019/04/19 17:00 | Marcos Giron v Sebastian Korda | 6-1,6-4 |
| Challenger Sarasota | 2019/04/18 21:00 | Sebastian Korda v Aleksandar Vukic | 6-4,2-6,6-4 |
| Challenger Sarasota | 2019/04/17 16:20 | James Ward v Sebastian Korda | 4-6,7-6,1-6 |