Round: 25 Ground: Clay
| ITF Italy F13 | 2016/05/31 13:05 | Giovanni Oradini v Matteo Viola | 4-6,7-5,4-6 |
| ITF Italy F23 Qual | 2016/08/01 10:45 | Manuel Bellutti v Giovanni Oradini | 4-6,6-2,3-6 |
| ITF Italy F23 Qual | 2016/07/30 07:30 | Lorenzo Schmid v Giovanni Oradini | 3-6,4-6 |
| ITF Italy F20 Qual | 2016/07/10 08:45 | Davide Pontoglio v Giovanni Oradini | 0-6,6-2,7-5 |
| ITF Italy F20 Qual | 2016/07/09 10:00 | Andrea Caligiana v Giovanni Oradini | 5-7,2-6 |
| ITF Italy F19 | 2016/07/03 09:40 | Gianluca Acquaroli v Giovanni Oradini | 0-6,6-4,6-4 |
| ITF Italy F19 | 2016/07/02 12:25 | Giuliano Benedetti v Giovanni Oradini | 1-6,0-6 |
| ITF Italy F15 | 2016/06/12 07:00 | Giovanni Oradini v Matteo De Vincentis | 3-6,3-6 |
| ITF Italy F15 | 2016/06/11 07:30 | Toby Martin v Giovanni Oradini | 6-7,6-4,1-6 |
| Challenger Recanati | 2016/07/19 14:50 | Matteo Viola v Ilya Ivashka | 3-6,1-6 |
| ATP Hamburg Qual | 2016/07/10 11:40 | Steven Diez v Matteo Viola | 6-4,6-4 |
| ATP Hamburg Qual | 2016/07/09 11:40 | Matteo Viola v Axel Michon | 6-2,6-1 |
| Challenger Bastad | 2016/07/04 09:45 | Matteo Viola v Grega Zemlja | 5-7,6-1,6-7 |
| ITF France F12 | 2016/06/29 10:00 | Caio Zampieri v Matteo Viola | 6-2,6-4 |
| ITF France F12 | 2016/06/28 13:50 | Matteo Viola v Zhizhen Zhang | 6-1,6-0 |
| Challenger Milan Qual | 2016/06/22 12:50 | Matteo Viola v Laslo Djere | 4-6,6-3,1-6 |
| Challenger Milan Qual | 2016/06/20 12:30 | Alejandro Gonzalez v Matteo Viola | 6-7,3-6 |