Stadium: Center Court Giorgi Round: 25 Ground: Clay
| ITF M15 Gubbio | 2019/07/16 10:30 | Federico Arnaboldi v Tommaso Roggero | 6-4,6-7,10-6 |
| Challenger Cordenons | 2019/08/14 17:00 | Federico Arnaboldi v Attila Balazs | 1-6,3-6 |
| Challenger Cordenons | 2019/08/12 11:05 | Riccardo Bonadio v Federico Arnaboldi | 1-6,6-7 |
| ITF M25 Appiano | 2019/08/09 10:00 | Federico Arnaboldi v Pietro Rondoni | 4-6,4-6 |
| ITF M25 Appiano | 2019/08/08 11:20 | Daniel Dutra Da Silva v Federico Arnaboldi | 4-6,6-4,5-7 |
| ITF M25 Appiano | 2019/08/06 09:30 | Federico Arnaboldi v Antonio Massara | 6-4,6-4 |
| ITF M25 Bolzano | 2019/08/01 08:30 | Denis Yevseyev v Federico Arnaboldi | 6-4,7-5 |
| ITF M25 Bolzano | 2019/07/30 10:10 | Federico Arnaboldi v Stefano Baldoni | 6-2,6-2 |
| ITF M25 Pontedera | 2019/07/25 10:45 | Gianluca Di Nicola v Federico Arnaboldi | 6-2,6-4 |
| ITF M25 Trieste | 2019/09/02 07:30 | Tommaso Roggero v Alexander Wolfschmidt | 6-1,6-1 |
| ITF M25 Trieste | 2019/09/01 13:10 | Manfred Fellin v Tommaso Roggero | 4-6,6-4,12-14 |
| ITF M15 Piombino | 2019/08/27 11:55 | Tommaso Roggero v Carlo Alberto Fossati | 6-3,2-6,7-10 |
| ITF M15 Piombino | 2019/08/26 13:15 | Giuseppe La Vela v Tommaso Roggero | 3-6,1-6 |
| ITF M25 Bolzano | 2019/07/29 13:25 | Paolo Dagnino v Tommaso Roggero | 7-5,2-6,11-9 |
| ITF M15 Gubbio | 2019/07/16 10:30 | Federico Arnaboldi v Tommaso Roggero | 6-4,6-7,10-6 |
| ITF M15 Gubbio | 2019/07/15 08:00 | Tommaso Roggero v Julien De Cuyper | 6-2,7-6 |
| ITF M25 Casinalbo | 2019/07/08 13:00 | Tommaso Roggero v Manuel Mazza | 2-6,6-7 |