Sergei Demekhine defeated Mikhail Ledovskikh 6-4 6-3 in the Russia F1 round of 32 on clay. The upset overturned the form book — Mikhail Ledovskikh came in leading the head-to-head 2–0, but Sergei Demekhine had been the form player, winning 2 of their last 4 on clay. Sergei Demekhine claimed a first win over Mikhail Ledovskikh in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-08-16 | Russia F2 | R32 | hard | Mikhail Ledovskikh | 6-7(2) 6-2 6-2 |
| 2004-08-09 | Russia F1 | R16 | clay | Mikhail Ledovskikh | 6-3 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.