John McEnroe defeated Andrei Cherkasov 6-1 4-6 6-4 in the Milan round of 32 on carpet. The result followed the form book — John McEnroe came in leading the head-to-head 2–1. John McEnroe extended 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 |
| 1991-05-27 | Roland Garros | R128 | clay | Andrei Cherkasov | 2-6 6-4 7-5 7-6 |
| 1990-09-24 | Basel | QF | hard | John McEnroe | 6-3 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.