Jean Noel Insausti defeated Vladimir Obradovic 6-3 6-4 in the Dominican Republic F2 qualifying round on hard. The upset overturned the form book — Vladimir Obradovic came in leading the head-to-head 1–0. Jean Noel Insausti claimed a first win over Vladimir Obradovic in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2007-12-03 | Dominican Republic F3 | R32 | hard | Vladimir Obradovic | 7-5 7-6(4) |