Ivan Sergeyev defeated Leonardo Tavares 6-4 6-2 in the Bulgaria F2 round of 16 on clay. The result followed the form book — Ivan Sergeyev came in leading the head-to-head 2–0. Ivan Sergeyev extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-09-19 | Davis Cup G2 F: UKR vs POR | RR | hard | Ivan Sergeyev | 7-6 4-6 6-3 |
| 2007-05-14 | Bulgaria F2 | QF | clay | Ivan Sergeyev | 6-4 4-6 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.