Michael Stich defeated Ivan Lendl 6-3 6-2 in the Hamburg quarter-final on clay. The upset overturned the form book — Ivan Lendl came in leading the head-to-head 5–0, defending last year's round of 32. Michael Stich claimed a first win over Ivan Lendl in six meetings, narrowing the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1993-04-26 | Munich | F | clay | Ivan Lendl | 7-6(2) 6-3 |
| 1991-08-26 | US Open | QF | hard | Ivan Lendl | 6-3 3-6 4-6 7-6(5) 6-1 |
| 1991-02-18 | Memphis | F | hard | Ivan Lendl | 7-5 6-3 |
| 1991-02-11 | Philadelphia | QF | hard | Ivan Lendl | 6-2 7-6(7) |
| 1990-08-27 | US Open | R64 | hard | Ivan Lendl | 6-4 5-7 6-3 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.