| Challenger Olbia | 10/15 12:20 | 14 | Kyrian Jacquet v Chandrasekar, Anirudh | 6-2,6-2 | |
| Challenger - Quimper | 01/23 16:00 | 14 | [217] Evan Furness v Chandrasekar, Anirudh [193] | 6-1,7-5 | |
| Challenger Nonthaburi | 01/15 03:00 | 14 | [200] Chandrasekar, Anirudh v Federico Gaio [421] | 0-6,3-6 | |
| Challenger Knoxville | 11/06 21:50 | 14 | [224] Chandrasekar, Anirudh v Tristan McCormick [492] | 2-6,2-6 | |
| Poznan, Poland | 05/29 09:00 | 14 | [278] Daniel Michalski v Chandrasekar, Anirudh [394] | 6-2,6-1 | |
| ITF M15 New Delhi | 03/23 04:00 | 25 | Singh, Digvijaypratap v Chandrasekar, Anirudh | 6-3,6-3 | |
| ITF M15 Bengaluru | 03/16 06:10 | 25 | Chandrasekar, Anirudh v Manish Sureshkumar | 4-6,3-6 | |
| ITF M15 Gurugram | 11/23 05:55 | 25 | Singh, Karunuday v Chandrasekar, Anirudh | 6-4,6-2 | |
| ITF M15 New Delhi | 11/17 04:00 | 25 | Philip Sekulic v Chandrasekar, Anirudh | 6-1,6-1 | |
| Challenger Losinj | 10/18 08:00 | 19 | Georgii Kravchenko v Chandrasekar, Anirudh | 6-0,6-1 | |
| Challenger Losinj | 10/17 11:00 | 14 | Eldin Nokic v Chandrasekar, Anirudh | 0-6,1-6 | |
| ITF M25 Setubal | 10/04 12:10 | 62 | Chandrasekar, Anirudh v Simone Vaccari | 2-6,4-6 | |
| Challenger Rennes | 09/12 13:30 | 14 | Chandrasekar, Anirudh v Titouan Droguet | 3-6,2-6 | |
| ITF M15 Allershausen | 08/31 08:00 | 54 | Chandrasekar, Anirudh v Weindl, Michael | 2-6,3-6 | |
| ITF M15 New Delhi | 03/28 05:00 | 44 | Chandrasekar, Anirudh v Siddharth Vishwakarma | 7-5,3-6,9-11 | |
| ITF M15 Pune | 03/22 07:30 | 54 | Chandrasekar, Anirudh v Qamar, Faisal | 4-6,6-3,15-17 | |
| ITF M15 Pune | 03/21 10:35 | 54 | Chandrasekar, Anirudh v Khandge, Kapeesh | 6-1,6-1 | |
| ITF M15 Indore | 03/09 04:00 | 25 | Manish Sureshkumar v Chandrasekar, Anirudh | 6-3,6-2 | |
| ITF M15 Lucknow | 03/02 04:45 | 25 | Sood, Lakshilt v Chandrasekar, Anirudh | 6-3,6-4 | |
| ITF - M15 Sharm El Sheikh | 02/15 07:30 | 62 | Crepaldi, Erik v Chandrasekar, Anirudh | 6-1,6-4 | |
| ITF - M15 Sharm El Sheikh | 02/14 07:00 | 62 | Chandrasekar, Anirudh v Okala, Noam | 6-4,2-6,10-4 | |
| ITF - M15 Sharm El Sheikh | 02/08 09:30 | 62 | Miladinovic, Marko v Chandrasekar, Anirudh | 6-3,6-4 | |
| ITF - M15 Sharm El Sheikh | 02/07 11:00 | 62 | Chandrasekar, Anirudh v Minarik, Kristof | 4-6,6-3,13-11 | |
| ITF - M15 Sharm El Sheikh | 01/31 09:00 | 62 | Chandrasekar, Anirudh v Nitin Kumar Sinha | 3-6,4-6 | |
| ITF M15 Cairo | 12/08 08:00 | 62 | Damien Wenger v Chandrasekar, Anirudh | Retired | |
| ITF M15 Cairo | 12/07 08:00 | 62 | Marcolini, Geronimo v Chandrasekar, Anirudh | 1-6,6-7 | |
| ITF M15 Cairo | 11/30 08:00 | 62 | Stefano Baldoni v Chandrasekar, Anirudh | 6-0,6-4 | |
| ITF M15 Cairo | 11/29 09:30 | 62 | Morsy, Omar v Chandrasekar, Anirudh | 2-6,3-6 | |
| ITF M15 Cairo | 11/23 11:30 | 62 | Stefano Baldoni v Chandrasekar, Anirudh | 6-1,6-0 | |
| ITF M15 Cairo | 11/22 09:00 | 62 | Connor, Preston v Chandrasekar, Anirudh | Retired |