Stadium: CENTRE COURT Round: 26 Ground: Clay
| ITF Italy F12 | 2016/05/28 13:00 | Marco Bortolotti v Stefanos Tsitsipas | 6-7,6-7 |
| ITF Italy F12 | 2016/05/27 13:00 | Claudio Fortuna v Stefanos Tsitsipas | 2-6,3-6 |
| ITF Italy F12 | 2016/05/26 18:40 | Stefanos Tsitsipas v Liam Caruana | 6-4,6-4 |
| ITF Italy F12 | 2016/05/25 12:05 | Laurynas Grigelis v Stefanos Tsitsipas | 1-6,4-6 |
| ITF Italy F12 | 2016/05/24 15:30 | Mate Valkusz v Stefanos Tsitsipas | 4-6,3-6 |
| ITF Italy F10 | 2016/05/14 09:30 | Stefanos Tsitsipas v Casper Ruud | 6-3,6-7,7-6 |
| ITF Italy F10 | 2016/05/13 08:30 | Andrea Pellegrino v Stefanos Tsitsipas | 2-6,4-6 |
| ITF Italy F10 | 2016/05/12 11:10 | Stefanos Tsitsipas v Jay Clarke | 6-2,6-3 |