Stadium: Court 1 Round: 27 Ground: Clay
| Challenger Vicenza | 2019/06/02 13:00 | Alessandro Giannessi v Filippo Baldi | 7-5,6-2 |
| Challenger Banja Luka | 2018/09/15 10:30 | Filippo Baldi v Alessandro Giannessi | 6-7,4-6 |
| Challenger Barcelona | 2019/10/03 10:30 | Filip Horansky v Alessandro Giannessi | 6-7,7-6,4-6 |
| Challenger Barcelona | 2019/10/02 09:00 | Ivan Nedelko v Alessandro Giannessi | 1-6,4-6 |
| Challenger Florence | 2019/09/26 14:05 | Philipp Kohlschreiber v Alessandro Giannessi | 4-6,6-4,6-3 |
| Challenger Florence | 2019/09/25 13:55 | Jules Okala v Alessandro Giannessi | 3-6,0-6 |
| Challenger Biella | 2019/09/20 12:50 | Alejandro Davidovich Fokina v Alessandro Giannessi | 6-2,6-1 |
| Challenger Biella | 2019/09/19 14:10 | Marco Trungelliti v Alessandro Giannessi | 6-7,1-6 |
| Challenger Biella | 2019/09/17 10:10 | Giacomo Dambrosi v Alessandro Giannessi | 4-6,4-6 |
| Challenger Szczecin | 2019/09/11 11:10 | Pawel Juszczak v Alessandro Giannessi | 6-2,6-0 |
| Challenger Barcelona | 2019/10/03 13:45 | Filippo Baldi v Jaume Pla Malfeito | 6-4,6-1 |
| Challenger Barcelona | 2019/10/01 09:25 | Filippo Baldi v Sandro Ehrat | 6-3,6-3 |
| Challenger Biella | 2019/09/17 13:35 | Peter Heller v Filippo Baldi | 3-6,6-4,7-5 |
| Challenger Banja Luka | 2019/09/11 09:40 | Zdenek Kolar v Filippo Baldi | 6-4,6-2 |
| Challenger Genova | 2019/09/05 10:00 | Guido Andreozzi v Filippo Baldi | 6-3,7-5 |
| Challenger Genova | 2019/09/04 11:35 | Filippo Baldi v Roberto Carballes Baena | 7-6,1-6,6-1 |
| Challenger Genova | 2019/09/02 14:55 | Rudolf Molleker v Filippo Baldi | 7-5,2-6,1-6 |
| Challenger Como | 2019/08/28 08:00 | Sadio Doumbia v Filippo Baldi | 3-6,7-6,6-2 |