Sandeep Kirtane defeated Rohan Bopanna 7-5 6-2 in the India 1 Masters 3 round of 16 on clay. The upset overturned the form book — Rohan Bopanna came in leading the head-to-head 1–0. Sandeep Kirtane claimed a first win over Rohan Bopanna in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-16 | India 2 Masters 1 | R16 | hard | Rohan Bopanna | 6-2 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.