Stadium: Center Court Round: 14 Ground: Hardcourt outdoor
| Challenger Perugia | 2021/07/05 16:30 | Salvatore Caruso v Luca Vanni | 7-6,6-4 |
| Challenger - Milan | 2021/06/22 12:05 | Jiri Lehecka v Luca Vanni | 6-3,7-6 |
| Challenger Forli | 2021/06/14 09:30 | Sebastian Fanselow v Luca Vanni | 2-6,6-2,7-5 |
| Challenger Forli | 2021/06/13 11:15 | Michele Vianello v Luca Vanni | 3-6,4-6 |
| ITF M15 Gaiba | 2021/06/09 12:25 | Antoine Bellier v Luca Vanni | 5-7,6-3,6-2 |
| Challenger Biella | 2021/05/31 11:05 | Luca Vanni v Camilo Ugo Carabelli | 2-6,2-6 |
| Challenger Biella | 2021/05/30 12:00 | Evgeny Karlovskiy v Luca Vanni | 3-6,1-6 |
| Challenger Biella | 2021/05/17 08:00 | Tomas Martin Etcheverry v Luca Vanni | 6-4,6-3 |
| Challenger Nur-Sultan | 2021/07/23 05:00 | Oleksii Krutykh v Nick Chappell | 3-6,6-3,7-5 |
| Challenger Nur-Sultan | 2021/07/21 06:30 | Nick Chappell v Sergiy Stakhovsky | 7-6,6-4 |
| Challenger Nur-Sultan | 2021/07/19 07:05 | Grigoriy Lomakin v Nick Chappell | 3-6,6-7 |
| Challenger Nur-Sultan | 2021/07/12 08:45 | Beibit Zhukayev v Nick Chappell | 4-6,6-3,7-6 |
| ITF M25 Nur-Sultan | 2021/07/07 05:10 | Sanjar Fayziev v Nick Chappell | 6-4,6-4 |
| ITF M25 Bakio | 2021/06/30 10:00 | Antoine Bellier v Nick Chappell | 3-6,6-4,6-4 |
| ATP Eastbourne | 2021/06/19 15:45 | Nick Chappell v Mikhail Kukushkin | 2-6,3-6 |
| Challenger Aix en Provence | 2021/06/13 08:30 | Nick Chappell v Sadio Doumbia | 0-6,4-6 |