Rupesh Roy defeated Vignesh Peranamallur-Chandrasekhar 6-4 7-6 in the Chennai q32 on hard. The result followed the form book — Rupesh Roy came in leading the head-to-head 2–1. Rupesh Roy extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2011-04-25 | India F5 | R32 | hard | Vignesh Peranamallur-Chandrasekhar | 6-3 6-1 |
| 2010-03-15 | India F1 | R32 | hard | Rupesh Roy | 6-2 6-1 |
| 2009-09-28 | India F10 | R16 | hard | Rupesh Roy | 4-6 6-3 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.