Round: 25 Ground: Clay
| ITF Italy F16 | 2016/06/21 14:00 | Francesco Picco v Andrea Guerrieri | 6-3,6-2 |
| ITF Italy F15 | 2016/06/15 11:30 | Markus Eriksson v Andrea Guerrieri | 6-2,6-3 |
| ITF Italy F15 | 2016/06/14 10:55 | Andrea Guerrieri v Filippo Baldi | 1-6,6-4,6-3 |
| ITF Croatia F1 | 2016/03/05 09:00 | Danilo Petrovic v Andrea Guerrieri | 6-1,7-6 |
| ITF Croatia F1 | 2016/03/04 08:30 | Luka Ilic v Andrea Guerrieri | 1-6,6-7 |
| ITF Croatia F1 | 2016/03/02 10:10 | Andrea Guerrieri v Ivan Bjelica | 6-4,7-5 |
| ITF Tunisia F7 | 2016/02/25 12:20 | Andrea Guerrieri v Walter Trusendi | 0-6,4-6 |
| ITF Tunisia F7 | 2016/02/24 13:55 | Louis Tessa v Andrea Guerrieri | 3-6,2-6 |
| ITF Italy F16 Qual | 2016/06/18 08:00 | Federico Maccari v Lorenzo Abbruciati | 3-6,5-7 |
| ITF Italy F15 | 2016/06/12 07:00 | Federico Maccari v Blake Ellis | 6-4,1-6,4-6 |
| ITF Italy F15 | 2016/06/11 07:30 | Federico Maccari v Daniele Chiurulli | 3-6,6-3,7-6 |
| ITF Italy F14 Qual | 2016/06/05 08:00 | Federico Maccari v Nicolo Turchetti | 3-6,6-2,3-6 |
| ITF Italy F13 | 2016/05/29 07:30 | Federico Maccari v Giovanni Oradini | 2-6,4-6 |
| ITF Ukraine F3 | 2016/05/25 07:00 | Volodymyr Uzhylovskyi v Federico Maccari | 6-4,6-7,6-3 |
| ITF Ukraine F2 | 2016/05/19 07:30 | Federico Maccari v Alexander Lebedyn | 4-6,6-4,4-6 |
| ITF Italy F6 | 2016/04/12 07:30 | Federico Maccari v Marvin Netuschil | 5-7,6-7 |