Jim Courier defeated Wayne Ferreira 4-6 7-6 7-5 6-4 in the Wimbledon round of 16 on grass. The result followed the form book — Jim Courier came in leading the head-to-head 6–0, defending last year's round of 32. Jim Courier extended the head-to-head to 7–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-02 | Canada Masters | R16 | hard | Jim Courier | 6-7 6-4 7-5 |
| 1997-02-10 | Dubai | QF | hard | Jim Courier | 6-2 7-5 |
| 1996-05-27 | Roland Garros | R16 | clay | Jim Courier | 4-6 6-1 6-3 6-3 |
| 1994-04-11 | Nice | QF | clay | Jim Courier | 6-3 6-2 |
| 1994-01-17 | Australian Open | R16 | hard | Jim Courier | 6-3 6-4 6-2 |
| 1991-05-27 | Roland Garros | R64 | clay | Jim Courier | 6-2 6-3 6-4 |
Averages over each player's completed matches in the selected window (147 vs 199). ATP, WTA & Challenger.
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About