Yevgeny Kafelnikov defeated Jim Courier 2-6 6-4 8-6 in the Grand Slam Cup quarter-final on carpet. The result followed the form book — Yevgeny Kafelnikov came in leading the head-to-head 3–1, defending last year's semi-final. Yevgeny Kafelnikov extended the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-01-18 | Australian Open | R32 | hard | Yevgeny Kafelnikov | 5-7 6-4 6-2 3-0 |
| 1998-04-04 | Davis Cup WG R1: USA vs RUS | RR | hard | Yevgeny Kafelnikov | 6-2 5-7 6-7 6-4 6-4 |
| 1994-06-13 | Halle | QF | grass | Yevgeny Kafelnikov | 6-1 6-4 |
| 1994-04-11 | Nice | R32 | clay | Jim Courier | 6-3 6-2 |
Averages over each player's completed matches in the selected window (200 vs 147). 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