Ivan Lendl defeated Pete Sampras 5-7 6-4 6-4 3-6 6-3 in the Philadelphia final on hard. The upset overturned the form book — Pete Sampras came in defending the title. Ivan Lendl extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1994-01-17 | Australian Open | R16 | hard | Pete Sampras | 7-6(5) 6-2 7-6(4) |
| 1993-02-15 | Philadelphia | SF | hard | Ivan Lendl | 7-6(4) 6-4 |
| 1990-08-27 | US Open | QF | hard | Pete Sampras | 6-4 7-6 3-6 4-6 6-2 |
| 1990-02-05 | Milan | SF | carpet | Ivan Lendl | 3-6 6-0 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.