Round: 25 Ground: Clay
| ITF Morocco F4 | 2016/07/27 09:00 | van Der Linden, Lennert v Chakrouni, Ayoub | 6-0,6-3 |
| ITF Morocco F4 | 2016/07/26 11:50 | Luis Lamelas, Manuel v Chakrouni, Ayoub | 2-6,3-6 |
| ITF Tunisia F21 | 2016/06/01 12:55 | Chakrouni, Ayoub v Lah, Sven | 7-5,2-6,6-7 |
| ITF Tunisia F21 | 2016/05/29 09:00 | Chakrouni, Ayoub v Jalil Saavedra, Naim Antonio | 6-2,4-6,6-1 |
| ITF Tunisia F20 | 2016/05/25 11:25 | Ghorbel, Anis v Chakrouni, Ayoub | 6-4,6-7,6-1 |
| ITF Tunisia F20 Qual | 2016/05/23 09:00 | Chakrouni, Ayoub v Naser, Javier | 7-5,6-3 |
| Tunisia F19, Singles Qualifying | 2016/05/20 14:05 | Chakrouni, Ayoub v Sousa, Pedro | 3-6,4-6 |
| Tunisia F19, Singles Qualifying | 2016/05/19 12:15 | Vibert, Francois Arthur v Chakrouni, Ayoub | 4-6,3-6 |
| ITF Spain F20 | 2016/07/04 13:15 | Chavez Villalpando, Luis Diego v Jaume Munar | 6-3,4-6,2-6 |
| ITF Spain F20 Qual | 2016/07/02 10:30 | Chavez Villalpando, Luis Diego v Morr, Jonathan | 6-0,6-2 |
| ITF Spain F19 | 2016/06/28 10:40 | Chavez Villalpando, Luis Diego v Ojeda Lara, Ricardo | 0-6,1-6 |
| ITF Spain F8 | 2016/04/04 08:00 | Ribeiro Navarrete, Samuel v Chavez Villalpando, Luis Diego | 6-3,6-1 |
| ITF Spain F8 | 2016/04/03 12:30 | Mardones, Bruno v Chavez Villalpando, Luis Diego | 2-6,4-6 |
| ITF Spain F7 | 2016/03/28 08:00 | Alex De Minaur v Chavez Villalpando, Luis Diego | 3-6,6-2,6-4 |
| ITF Spain F7 | 2016/03/26 08:30 | Grigoriu, Patrick v Chavez Villalpando, Luis Diego | 5-7,5-7 |
| ITF France F6 | 2016/03/15 13:00 | Chavez Villalpando, Luis Diego v Gunneswaran, Prajnesh | 6-3,3-6,1-6 |