Stadium: Court 6 Round: 44 Ground: Clay
| ITF M15 Ulcinj | 2021/09/12 08:00 | Felipe Mikkelsen v Leonardo Rossi | 2-6,1-6 |
| ITF M25 Lesa | 2021/08/22 07:00 | Leonardo Rossi v Edoardo Zanada | 0-6,3-6 |
| ITF M15 Warmbad-Villach | 2021/08/17 13:00 | Franco Ribero v Leonardo Rossi | 3-6,6-4,10-4 |
| ITF M15 Warmbad-Villach | 2021/08/16 12:30 | Leonardo Rossi v Michalis Sakellaridis | 7-6,6-4 |
| ITF M25 Bolzano | 2021/08/02 07:05 | Augusto Virgili v Leonardo Rossi | 6-4,3-6,10-8 |
| ITF M25 Ajaccio | 2021/07/04 15:30 | Clement Chidekh v Leonardo Rossi | 6-3,6-2 |
| ITF M15 Cairo | 2021/04/25 12:30 | Leonardo Rossi v Olexiy Kolisnyk | 5-7,6-1,2-10 |
| ITF M15 Cairo | 2021/04/19 09:30 | Leonardo Rossi v Benedikt Henning | 6-7,4-6 |
| ITF M15 Ulcinj | 2021/09/08 09:55 | Gabriele Piraino v Edoardo Lavagno | 6-7,2-6 |
| ITF M15 Ulcinj | 2021/09/06 13:00 | Gabriele Piraino v Tomislav Jotovski | 6-3,6-0 |
| ITF M15 Ulcinj | 2021/09/06 07:30 | Gabriele Piraino v Horst Rieder | 7-6,6-1 |
| Challenger Como | 2021/08/29 14:45 | Gabriele Piraino v Franco Agamenone | 2-6,2-6 |
| Challenger Barletta | 2021/08/23 11:00 | Andrea Vavassori v Gabriele Piraino | 6-2,5-7,6-3 |
| Challenger Barletta | 2021/08/22 14:45 | Gabriele Piraino v Alvaro Lopez San Martin | 7-6,3-6,7-5 |
| ITF M15 Pescara | 2021/08/17 10:25 | Gabriele Piraino v Alexis Musialek | 4-6,2-6 |
| Challenger Cordenons | 2021/08/02 11:55 | Alejandro Gonzalez v Gabriele Piraino | 6-3,6-2 |