Round: 25 Ground: Hardcourt indoor
| ITF Great Britain F5 | 2016/10/31 10:00 | Aidan Mchugh v Max Stewart | 7-6,7-5 |
| ITF Spain F14 Qual | 2016/05/15 08:00 | Zeljko Milovic v Max Stewart | 6-4,6-1 |
| ITF Spain F14 Qual | 2016/05/14 07:00 | Max Stewart v Alejandro Reguant | 6-4,6-1 |
| Challenger Andria | 2016/11/22 18:30 | Alessandro Bega v Andrea Pellegrino | 7-5,2-6,7-6 |
| ITF Italy F35 | 2016/10/25 08:40 | Andrea Pellegrino v Andrea Guerrieri | 5-7,4-6 |
| Challenger Casablanca Qual | 2016/10/08 14:55 | Andrea Pellegrino v Lennert V. D Linden | 5-7,3-6 |
| Challenger Casablanca Qual | 2016/10/08 10:30 | Antonio Sancic v Andrea Pellegrino | 4-6,4-6 |
| Challenger Mohammedia Qual | 2016/10/01 13:35 | Mario Vilella Martinez v Andrea Pellegrino | 6-1,6-4 |
| Challenger Rome 2 | 2016/09/26 11:30 | Federico Gaio v Andrea Pellegrino | 6-1,3-6,6-2 |
| ITF Italy F29 | 2016/09/14 10:50 | Nicola Ghedin v Andrea Pellegrino | 7-5,6-1 |
| ITF Italy F29 | 2016/09/12 07:30 | David Simunek v Andrea Pellegrino | 1-6,5-7 |