Rupesh Roy defeated Karan Rastogi 6-4 6-4 in the India F1 qualifying round on hard. The upset overturned the form book — Karan Rastogi came in leading the head-to-head 2–0. Rupesh Roy claimed a first win over Karan Rastogi in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2011-08-08 | Kazakhstan F5 | R16 | hard | Karan Rastogi | 4-6 6-1 6-0 |
| 2011-04-18 | India F4 | R16 | hard | Karan Rastogi | 7-6(3) 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.