Stadium: Court Central Round: 14 Ground: Clay
| Challenger Barcelona | 2020/10/06 08:00 | Peter Polansky v Alessandro Giannessi | 2-6,4-6 |
| ATP Quito | 2018/02/07 17:00 | Alessandro Giannessi v Peter Polansky | 6-3,6-4 |
| Challenger Prague | 2021/05/02 15:15 | Denis Istomin v Peter Polansky | 6-3,7-5 |
| Challenger Ostrava | 2021/04/27 10:00 | Peter Polansky v Lukas Klein | 3-6,5-7 |
| Challenger Tallahassee | 2021/04/19 19:10 | Peter Polansky v Michael Mmoh | 5-7,6-7 |
| Challenger Orlando | 2021/04/13 15:20 | Peter Polansky v Yasutaka Uchiyama | 3-6,6-3,4-6 |
| Challenger Nur-Sultan | 2021/03/04 05:00 | Soonwoo Kwon v Peter Polansky | 7-6,6-4 |
| Challenger Nur-Sultan | 2021/02/23 10:10 | Peter Polansky v Maximilian Marterer | 3-6,4-6 |
| Challenger Potchefstroom | 2021/02/16 08:00 | Ulises Blanch v Peter Polansky | 7-6,6-3 |
| Challenger Potchefstroom | 2021/02/12 09:00 | Peter Polansky v Nick Chappell | 4-6,7-6,4-6 |
| Challenger Heilbronn | 2021/05/12 13:15 | Alessandro Giannessi v Daniel Elahi Galan | 7-6,6-7,4-6 |
| Challenger Heilbronn | 2021/05/10 15:40 | Alessandro Giannessi v Prajnesh Gunneswaran | 7-6,6-1 |
| Challenger Biella | 2021/05/04 08:00 | Alessandro Giannessi v Juan Pablo Varillas | 4-6,5-7 |
| Challenger Rome | 2021/05/01 12:45 | Alessandro Giannessi v Juan Manuel Cerundolo | 6-4,4-6,5-7 |
| Challenger Rome | 2021/04/30 11:20 | Alessandro Giannessi v Thanasi Kokkinakis | 7-5,3-6,7-5 |
| Challenger Rome | 2021/04/28 11:20 | Alessandro Giannessi v Jay Clarke | 6-2,6-4 |
| Challenger Rome | 2021/04/26 11:05 | Alessandro Giannessi v Guido Andreozzi | 6-3,6-3 |
| Challenger Belgrade | 2021/04/12 11:20 | Alessandro Giannessi v Maxime Janvier | 3-6,6-4,6-4 |