Round: 62 Ground: Clay
| ITF Italy F1 Qual | 2016/02/27 08:30 | Maccari, Federico v Giovanni Oradini | 6-4,6-4 |
| ITF Italy F32 Qual | 2014/09/13 10:00 | Maccari, Federico v Giovanni Oradini | 7-6,6-0 |
| ITF Ukraine F3 | 2016/05/25 07:00 | Uzhylovsky, Vladimir v Maccari, Federico | 6-4,6-7,6-3 |
| ITF Ukraine F2 | 2016/05/19 07:30 | Maccari, Federico v Lebedyn, Alexander | 4-6,6-4,4-6 |
| ITF Italy F6 | 2016/04/12 07:30 | Maccari, Federico v Netuschil, Marvin | 5-7,6-7 |
| ITF Italy F6 Qual | 2016/04/10 08:00 | Maccari, Federico v Borroni, Andrea | 7-6,6-3 |
| Italie F3, Simples | 2016/03/15 09:30 | Maccari, Federico v Eriksson, Markus | 3-6,3-6 |
| Italie F3, Qualifications Simples | 2016/03/13 11:10 | Maccari, Federico v Virgili, Augusto | 6-2,6-4 |
| Italie F3, Qualifications Simples | 2016/03/12 14:00 | Maccari, Federico v Hermans, Mats | 6-3,6-4 |
| ITF Italy F2 Qual | 2016/03/05 09:30 | Maccari, Federico v Gijs Brouwer | 4-6,6-1,5-7 |
| ITF Italy F13 | 2016/05/28 08:00 | Giovanni Oradini v Longo, Michele | 6-3,6-7,6-3 |
| Challenger Vicenza Qual | 2016/05/21 14:45 | Petrovic, Danilo v Giovanni Oradini | 6-1,6-1 |
| ITF Italy F11 | 2016/05/18 13:40 | Baldi, Filippo v Giovanni Oradini | 6-1,7-5 |
| Italie F11, Qualifications Simples | 2016/05/16 14:35 | Giovanni Oradini v Bessire, Francesco | 6-4,6-3 |
| Italie F11, Qualifications Simples | 2016/05/16 10:25 | Raul Brancaccio v Giovanni Oradini | 3-6,4-6 |
| Italie F11, Qualifications Simples | 2016/05/15 14:05 | Giovanni Oradini v de Carlo, Giacomo | 6-1,6-0 |
| ITF Italy F9 | 2016/05/03 10:15 | Bensoussan, Samuel v Giovanni Oradini | 6-4,6-3 |
| ITF Italy F9 Qual | 2016/05/01 08:00 | Giovanni Oradini v Giovanni Calvano | 6-0,6-3 |