Ajay Ramaswami advanced when Sunil Kumar retired 2-0 in the India 1 2 round of 16. Ajay Ramaswami extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-11-08 | India 2 Satellite 3 | R32 | clay | Sunil Kumar | 6-4 6-1 |
| 2002-11-11 | India F8 | R32 | hard | Ajay Ramaswami | 6-4 6-3 |
| 2002-06-24 | Canada F3 | R16 | hard | Sunil Kumar | 7-5 6-4 |
| 2001-10-15 | India F4 | QF | hard | Ajay Ramaswami | 2-6 6-4 7-6(2) |