Stadium: Court 1 Round: 24 Ground: Hardcourt indoor
| Davis Cup | 2019/09/14 10:15 | Benjamin Hassan v Sanjar Fayziev | 2-6,6-3,6-4 |
| Davis Cup | 2019/09/13 11:15 | Benjamin Hassan v Khumoyun Sultanov | 2-6,6-3,7-5 |
| Challenger Meerbusch | 2019/08/15 11:00 | Carlos Taberner v Benjamin Hassan | 7-6,6-3 |
| Challenger Augsburg | 2019/08/08 09:00 | Benjamin Hassan v Facundo Mena | 6-4,1-6,0-6 |
| Challenger Augsburg | 2019/08/06 14:30 | Lukas Rosol v Benjamin Hassan | 4-6,4-6 |
| Challenger Augsburg | 2019/08/05 11:05 | Tak Khunn Wang v Benjamin Hassan | 2-6,4-6 |
| Challenger Tampere | 2019/07/24 09:35 | Kimmer Coppejans v Benjamin Hassan | 6-3,6-3 |
| Challenger Tampere | 2019/07/22 13:30 | Panu Virtanen v Benjamin Hassan | 6-7,1-6 |
| Challenger Portoroz | 2019/08/14 16:40 | Luca Vanni v Artem Dubrivnyy | 6-7,6-4,4-6 |
| Challenger Segovia | 2019/07/31 18:55 | Hugo Grenier v Luca Vanni | 7-6,6-3 |
| Challenger Prag | 2019/07/24 13:30 | Carlos Taberner v Luca Vanni | 6-2,6-4 |
| Challenger San Benedetto | 2019/07/16 19:15 | Andrea Pellegrino v Luca Vanni | 7-5,6-4 |
| Challenger Perugia | 2019/07/09 10:15 | Oriol Roca Batalla v Luca Vanni | 7-6,6-2 |
| Challenger Recanati | 2019/07/01 17:30 | Luca Vanni v Alen Avidzba | 6-7,4-6 |
| Wimbledon | 2019/06/24 10:00 | Christopher Eubanks v Luca Vanni | 7-6,3-6,6-3 |
| ATP Miami | 2019/03/18 16:00 | Felix Auger Aliassime v Luca Vanni | 4-6,6-4,6-1 |