Navdeep Singh defeated Ranjeet Virali Murugesan 6-4 6-7 6-2 in the India F1 round of 32 on hard. The upset overturned the form book — Ranjeet Virali Murugesan came in leading the head-to-head 2–1. Navdeep Singh 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 |
| 2009-03-23 | India F2 | R32 | clay | Ranjeet Virali Murugesan | 6-4 0-6 6-0 |
| 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.