Stadium: Court 2 Round: 25 Ground: Clay
| ITF M15 Ulcinj | 2021/09/20 11:30 | Leonardo Rossi v Flemming Peters | 6-3,6-2 |
| ITF M15 Ulcinj | 2021/09/20 08:00 | Lior Goldenberg v Leonardo Rossi | 1-6,1-6 |
| ITF M15 Ulcinj | 2021/09/19 08:00 | Stefano Reitano v Leonardo Rossi | 2-6,6-4,6-10 |
| ITF M15 Ulcinj | 2021/09/13 08:00 | Leonardo Rossi v Gabriele Piraino | 2-6,1-6 |
| 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 M15 Ulcinj | 2021/09/09 08:25 | Antonio Massara v Mariano Navone | 1-6,2-6 |
| ITF M15 Ulcinj | 2021/09/07 10:55 | Karl Friberg v Antonio Massara | 2-6,3-6 |
| ITF M15 Ulcinj | 2021/09/02 08:30 | Antonio Massara v Gergely Madarasz | 3-6,1-6 |
| ITF M15 Ulcinj | 2021/09/01 13:40 | Ioannis Xilas v Antonio Massara | 6-3,3-6,3-6 |
| ITF M25 Lesa | 2021/08/25 12:30 | Federico Arnaboldi v Antonio Massara | 6-2,6-2 |
| ITF M15 Pescara | 2021/08/18 12:10 | Antonio Massara v Riccardo Balzerani | 4-6,3-6 |
| ITF M15 Monastir | 2021/08/05 07:30 | Antonio Massara v Luca Potenza | 6-4,1-6,3-6 |
| ITF M15 Monastir | 2021/07/27 08:00 | Antonio Massara v Rishab Agarwal | 6-4,2-6,4-6 |