Stadium: Court 1 Round: 14 Ground: Clay
| ITF M25 Setubal | 2021/10/04 12:10 | Chandrasekar, Anirudh v Simone Vaccari | 2-6,4-6 |
| Challenger Rennes | 2021/09/12 13:30 | Chandrasekar, Anirudh v Titouan Droguet | 3-6,2-6 |
| ITF M15 Allershausen | 2021/08/31 08:00 | Chandrasekar, Anirudh v Weindl, Michael | 2-6,3-6 |
| ITF M15 New Delhi | 2021/03/28 05:00 | Chandrasekar, Anirudh v Siddharth Vishwakarma | 7-5,3-6,9-11 |
| ITF M15 Pune | 2021/03/22 07:30 | Chandrasekar, Anirudh v Qamar, Faisal | 4-6,6-3,15-17 |
| ITF M15 Pune | 2021/03/21 10:35 | Chandrasekar, Anirudh v Khandge, Kapeesh | 6-1,6-1 |
| ITF M15 Indore | 2021/03/09 04:00 | Manish Sureshkumar v Chandrasekar, Anirudh | 6-3,6-2 |
| ITF M15 Lucknow | 2021/03/02 04:45 | Sood, Lakshilt v Chandrasekar, Anirudh | 6-3,6-4 |