Stadium: Court 5 Round: 54 Ground: Clay
| ITF M25 Santa Margherita | 2019/04/08 12:00 | Giacomo Dambrosi v Victor Vlad Cornea | 3-6,5-7 |
| ITF M25 Santa Margherita | 2019/04/01 12:00 | Giacomo Dambrosi v Omar Giacalone | 1-6,3-6 |
| ITF M25 Santa Margherita | 2019/03/25 16:00 | Gianluca Di Nicola v Giacomo Dambrosi | 6-1,6-2 |
| ITF M25 Trento | 2019/02/25 09:00 | Felix Corwin v Giacomo Dambrosi | 3-6,6-1,10-5 |
| ITF M15 Monastir | 2019/02/18 08:00 | Giacomo Dambrosi v Yanais Laurent | 0-6,1-6 |
| Challenger Andria | 2018/11/17 13:00 | Giacomo Dambrosi v Alexander Lazov | 6-7,1-6 |
| ITF Italy F27 | 2018/09/08 12:00 | Mauro De Maio v Giacomo Dambrosi | 6-4,6-1 |
| ITF Italy F26 | 2018/09/04 14:30 | Lorenzo Brunetti v Giacomo Dambrosi | 6-4,5-7,6-3 |
| ITF M15 Antalya | 2019/04/02 07:00 | Georg Winkler v Damien Wenger | 3-6,2-6 |
| ITF M15 Antalya | 2019/04/01 07:00 | Georg Winkler v Bulat Galiev | 6-1,6-2 |
| ITF M15 Antalya | 2019/03/26 09:50 | Georg Winkler v Felipe Meligeni Rodrigues Alves | 0-6,2-6 |
| ITF M15 Antalya | 2019/03/21 09:10 | Pietro Rondoni v Georg Winkler | 7-6,1-6,6-1 |
| ITF M15 Antalya | 2019/03/20 10:00 | Sandro Kopp v Georg Winkler | 6-1,4-6,3-6 |
| ITF M15 Antalya | 2019/03/19 09:15 | Georg Winkler v Shamael Chaudhry | 6-2,6-4 |
| ITF M15 Antalya | 2019/03/18 07:15 | Georg Winkler v Jim Walder | 6-2,6-4 |
| ITF M15 Antalya | 2019/02/01 08:45 | Wilson Leite v Georg Winkler | 7-6,6-2 |