Ranjeet Virali Murugesan defeated Navdeep Singh 6-4 0-6 6-0 in the India F2 round of 32 on clay. The upset overturned the form book — Navdeep Singh came in leading the head-to-head 2–1. Ranjeet Virali Murugesan narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-05-18 | Kuwait F1 | R32 | hard | Ranjeet Virali Murugesan | 7-5 6-3 |
| 2009-03-16 | India F1 | R32 | hard | Navdeep Singh | 6-4 6-7(5) 6-2 |
| 2005-05-30 | India 1 1 | R32 | hard | Navdeep Singh | 6-4 4-6 7-6(8) |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.