Ajay Malik defeated Deepak Anantharamu 6-4 6-0 in the M25 Kalaburagi 1 q32 on hard. The upset overturned the form book — Deepak Anantharamu came in leading the head-to-head 1–0. Ajay Malik claimed a first win over Deepak Anantharamu in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2023-03-26 | M25 Mysuru 1 | Q32 | hard | Deepak Anantharamu | 7-6(2) 7-6(8) |