Vignesh Peranamallur-Chandrasekhar defeated Rupesh Roy 6-3 6-1 in the India F5 round of 32 on hard. The upset overturned the form book — Rupesh Roy came in leading the head-to-head 3–0. Vignesh Peranamallur-Chandrasekhar claimed a first win over Rupesh Roy in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2011-01-01 | Chennai | Q32 | hard | Rupesh Roy | 6-4 7-6(6) |
| 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.