Dmitri Sitak defeated Pavel Ivanov 5-7 7-5 6-2 in the Jamaica F4 round of 16 on hard. The upset overturned the form book — Pavel Ivanov came in leading the head-to-head 1–0. Dmitri Sitak claimed a first win over Pavel Ivanov in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-05-08 | Uzbekistan F4 | SF | hard | Pavel Ivanov | 4-6 6-2 6-4 |