Murad Inoyatov defeated Ivan Sergeyev 7-6 7-6 in the Egypt F2 round of 32 on clay. The upset overturned the form book — Ivan Sergeyev came in leading the head-to-head 4–0. Murad Inoyatov claimed a first win over Ivan Sergeyev in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-07-20 | Georgia F2 | QF | clay | Ivan Sergeyev | 6-2 6-2 |
| 2009-03-30 | Turkey F3 | QF | clay | Ivan Sergeyev | 6-4 6-3 |
| 2009-03-23 | Turkey F2 | QF | clay | Ivan Sergeyev | 6-3 6-0 |
| 2004-07-05 | Ukraine F3 | R32 | clay | Ivan Sergeyev | 6-3 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.