Andrei Cherkasov defeated John McEnroe 2-6 6-4 7-5 7-6 in the Roland Garros round of 128 on clay. The upset overturned the form book — John McEnroe came in leading the head-to-head 3–0. Andrei Cherkasov claimed a first win over John McEnroe in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1992-01-13 | Australian Open | R64 | hard | John McEnroe | 7-5 3-6 6-4 6-3 |
| 1990-09-24 | Basel | QF | hard | John McEnroe | 6-3 7-5 |
| 1990-02-05 | Milan | R32 | carpet | John McEnroe | 6-1 4-6 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.