Stadium: Center Round: 29 Ground: Clay
| Challenger Bergamo | 2020/02/17 16:55 | Giulio Zeppieri v Flavio Cobolli | 6-3,3-6,7-6 |
| Challenger Rome | 2021/05/02 09:00 | Flavio Cobolli v Juan Manuel Cerundolo | 2-6,6-3,3-6 |
| Challenger Rome | 2021/05/01 13:00 | Cem Ilkel v Flavio Cobolli | 3-6,5-7 |
| Challenger Rome | 2021/04/30 12:55 | Flavio Cobolli v Andrea Pellegrino | 7-6,6-1 |
| Challenger Rome | 2021/04/29 08:00 | Danilo Petrovic v Flavio Cobolli | 2-6,2-6 |
| Challenger Rome | 2021/04/27 08:00 | Flavio Cobolli v Steven Diez | 6-4,6-1 |
| Challenger Rome | 2021/04/22 09:00 | Andrea Pellegrino v Flavio Cobolli | 7-6,6-1 |
| Challenger Rome | 2021/04/20 08:00 | Flavio Cobolli v Hugo Grenier | 6-1,4-6,6-2 |
| Challenger Rome | 2021/04/18 13:05 | Tobias Kamke v Flavio Cobolli | 6-2,4-6,5-7 |
| Challenger Rome | 2021/04/30 11:40 | Juan Manuel Cerundolo v Giulio Zeppieri | 6-0,6-3 |
| Challenger Rome | 2021/04/28 09:30 | Felipe Meligeni Rodrigues Alves v Giulio Zeppieri | 4-6,3-6 |
| Challenger Rome | 2021/04/26 12:25 | Giulio Zeppieri v Hugo Dellien | 1-6,6-3,6-4 |
| Challenger Rome | 2021/04/22 09:00 | Giulio Zeppieri v Sebastian Ofner | 3-6,5-7 |
| Challenger Rome | 2021/04/20 11:20 | Giulio Zeppieri v Stefano Napolitano | 6-3,6-4 |
| ATP Cagliari | 2021/04/05 15:50 | Aljaz Bedene v Giulio Zeppieri | 1-6,7-5,7-6 |
| Challenger Lille | 2021/03/25 09:30 | Jonas Forejtek v Giulio Zeppieri | 6-3,6-4 |
| Challenger Lille | 2021/03/24 10:30 | Giulio Zeppieri v Oscar Otte | 7-6,6-3 |