Round: 44 Ground: Clay
| ITF Morocco F8 | 2016/10/31 12:15 | Kristijan Mesaros v Ayoub Chakrouni | 6-0,6-0 |
| Challenger Casablanca Qual | 2016/10/08 10:10 | Dino Marcan v Ayoub Chakrouni | 6-1,6-0 |
| Challenger Mohammedia Qual | 2016/10/01 09:00 | Ayoub Chakrouni v Gibril Diarra | 1-6,1-6 |
| Challenger Meknes | 2016/09/13 10:00 | Omar Salman v Ayoub Chakrouni | 6-1,6-1 |
| ITF Morocco F6 | 2016/08/09 22:00 | Gianni Mina v Ayoub Chakrouni | 6-1,6-0 |
| ITF Morocco F6 | 2016/08/07 22:00 | Mohamed Hassan v Ayoub Chakrouni | 3-6,0-6 |
| ITF Morocco F5 | 2016/08/02 22:00 | Sherif Sabry v Ayoub Chakrouni | 1-6,6-0,6-3 |
| ITF Morocco F5 | 2016/08/01 22:00 | Ayoub Chakrouni v Luis Diego Chavez Villalpando | 7-6,6-2 |
| ITF Tunisia F3 | 2017/01/21 09:00 | Ludovico Scerrati v Tommaso Gabrieli | 0-6,1-6 |
| ITF Tunisia F2 | 2017/01/18 08:00 | Tommaso Gabrieli v Attila Balazs | 0-6,2-6 |
| ITF Tunisia F1 | 2017/01/11 08:00 | Tommaso Gabrieli v Goncalo Oliveira | 4-6,3-6 |
| ITF Tunisia F27 | 2016/10/10 11:00 | Gregorio Lulli v Tommaso Gabrieli | 6-3,6-4 |
| ITF Tunisia F27 | 2016/10/09 11:00 | Christian Felline v Tommaso Gabrieli | 0-6,0-6 |
| ITF Ukraine F4 Qual | 2016/09/19 09:10 | Tommaso Gabrieli v Igor Karpovets | 2-6,6-1,3-6 |
| ITF Serbia F7 | 2016/09/13 08:00 | Alexandar Lazarov v Tommaso Gabrieli | 6-4,3-6,6-4 |
| ITF Serbia F7 Qual | 2016/09/12 08:00 | Tommaso Gabrieli v Rajko Mladenovic | 7-6,6-3 |