Stadium: Center Round: 29 Ground: Clay
| Challenger Forli | 2021/06/14 11:15 | Flavio Cobolli v Giulio Zeppieri | 6-0,7-5 |
| Challenger Bergamo | 2020/02/17 16:55 | Giulio Zeppieri v Flavio Cobolli | 6-3,3-6,7-6 |
| Challenger Verona | 2021/08/16 09:00 | Flavio Cobolli v Matija Pecotic | 3-6,4-6 |
| Challenger Verona | 2021/08/15 10:00 | Flavio Cobolli v Alessio Zanotti | 6-1,6-4 |
| Challenger Trieste | 2021/07/30 17:00 | Timofey Skatov v Flavio Cobolli | 6-7,6-1,7-6 |
| Challenger Trieste | 2021/07/28 14:45 | Flavio Cobolli v Antoine Hoang | 6-2,6-1 |
| Challenger Trieste | 2021/07/27 13:00 | Flavio Cobolli v Michael Vrbensky | 7-6,6-3 |
| ATP Umag | 2021/07/18 14:00 | Daniel Altmaier v Flavio Cobolli | 2-6,6-3,6-1 |
| Challenger Todi | 2021/07/16 17:00 | Federico Gaio v Flavio Cobolli | 7-5,6-4 |
| Challenger Todi | 2021/07/14 16:05 | Flavio Cobolli v Andrea Collarini | 6-4,6-3 |
| Challenger Verona | 2021/08/18 13:00 | Giulio Zeppieri v Dmitry Popko | 5-7,6-2,2-6 |
| Challenger Verona | 2021/08/16 11:30 | Vitaliy Sachko v Giulio Zeppieri | 6-1,5-7,2-6 |
| Challenger San Marino | 2021/08/08 08:00 | Giulio Zeppieri v Vladyslav Orlov | 7-5,4-6,4-6 |
| Challenger Cordenons | 2021/08/06 11:00 | Francisco Cerundolo v Giulio Zeppieri | 6-1,4-6,6-3 |
| Challenger Cordenons | 2021/08/04 09:00 | Giulio Zeppieri v Riccardo Bonadio | 6-3,6-2 |
| Challenger Cordenons | 2021/08/03 10:25 | Andrea Pellegrino v Giulio Zeppieri | 7-5,6-7,6-7 |
| Challenger Cordenons | 2021/08/02 09:00 | Giulio Zeppieri v Nicolas Kicker | 7-6,6-0 |
| Challenger Cordenons | 2021/08/01 09:30 | Giulio Zeppieri v Martin Cuevas | 6-3,6-1 |