Kirill Ivanov Smolensky defeated Maxime Boye 5-7 6-4 6-3 in the Portugal 2 Masters 2 round of 32 on carpet. The result followed the form book — Kirill Ivanov Smolensky came in leading the head-to-head 1–0. Kirill Ivanov Smolensky extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-02 | Portugal 2 Masters 3 | R16 | carpet | Kirill Ivanov Smolensky | 6-4 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.