| ATP - Antalya | 01/07 07:00 | 19 | [278] Andrea Pellegrino v Dimitar Kuzmanov [298] | 6-4,6-7,5-7 | |
| ATP - Antalya | 01/06 10:00 | 168 | Andrea Pellegrino v Cengiz Aksu | 3-6,6-2,6-0 | |
| Challenger - Ortisei | 11/16 13:00 | 25 | [138] Federico Gaio v Andrea Pellegrino [277] | 6-3,6-4 | |
| Challenger - Ortisei | 11/15 11:20 | 19 | Evgeny Karlovskiy v Andrea Pellegrino | 6-7,6-0,2-6 | |
| Challenger - Ortisei | 11/14 14:00 | 64 | Erwin Trobinger v Andrea Pellegrino | 4-6,0-6 | |
| Challenger - Parma 2 | 11/03 14:05 | 25 | [141] Cedrik-Marcel Stebe v Andrea Pellegrino [275] | 3-6,6-4,6-4 | |
| Challenger - Marbelha | 10/27 10:00 | 25 | [274] Andrea Pellegrino v Daniel Elahi Galan [132] | 3-6,2-6 | |
| Challenger - Marbelha | 10/26 10:00 | 164 | [292] Andrea Arnaboldi v Andrea Pellegrino [274] | 6-3,4-6,2-6 | |
| Challenger - Marbelha | 10/25 09:30 | 19 | [322] Inigo Cervantes v Andrea Pellegrino [274] | 5-7,7-6,4-6 | |
| ATP - Sardenha | 10/15 09:20 | 26 | [143] Lorenzo Musetti v Andrea Pellegrino [292] | 6-2,6-1 | |
| ATP - Sardenha | 10/12 13:45 | 25 | [292] Andrea Pellegrino v Stefano Travaglia [70] | Retired | |
| ATP - Sardenha | 10/11 08:00 | 164 | [296] Andrea Pellegrino v Danilo Petrovic [160] | 7-6,3-6,6-2 |