Gaetan De Lovinfosse defeated Rupesh Roy 6-1 6-3 in the India F5 round of 16 on clay. The upset overturned the form book — Rupesh Roy came in leading the head-to-head 2–0. Gaetan De Lovinfosse claimed a first win over Rupesh Roy in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2012-04-16 | India F4 | R32 | clay | Rupesh Roy | 7-6(4) 6-1 |
| 2010-11-22 | Dominican Republic F1 | R32 | hard | Rupesh Roy | 6-3 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.