Alexander Sikanov defeated Kirill Ivanov Smolensky 6-1 6-1 in the Russia F2 round of 32 on clay. The upset overturned the form book — Kirill Ivanov Smolensky came in leading the head-to-head 1–0. Alexander Sikanov claimed a first win over Kirill Ivanov Smolensky in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-29 | Bangladesh F2 | R16 | hard | Kirill Ivanov Smolensky | 6-2 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.