Mihail Kanev defeated Nenad Zimonjic 7-5 7-6 in the Yugoslavia Macedonia Masters 1 qualifying round on clay. The upset overturned the form book — Nenad Zimonjic came in leading the head-to-head 2–0. Mihail Kanev claimed a first win over Nenad Zimonjic in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-06-01 | Bulgaria Macedonia Masters 3 | QF | clay | Nenad Zimonjic | 6-3 6-1 |
| 1995-05-13 | Bulgaria Macedonia Masters 3 | R32 | clay | Nenad Zimonjic | 6-4 3-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.