Andre Agassi defeated Yevgeny Kafelnikov 6-3 7-6 6-4 in the US Open round of 32 on hard. The result followed the form book — Andre Agassi came in leading the head-to-head 5–2, defending last year's final. Andre Agassi extended the head-to-head to 6–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-11-27 | Masters Cup | RR | hard | Andre Agassi | 6-1 6-4 |
| 2000-01-17 | Australian Open | F | hard | Andre Agassi | 3-6 6-3 6-2 6-4 |
| 1999-11-22 | Tour Finals | SF | hard | Andre Agassi | 6-4 7-6(5) |
| 1999-08-30 | US Open | SF | hard | Andre Agassi | 1-6 6-3 6-3 6-3 |
| 1999-08-16 | Washington | F | hard | Andre Agassi | 7-6(3) 6-1 |
| 1999-08-02 | Canada Masters | SF | hard | Yevgeny Kafelnikov | 6-1 6-4 |
| 1998-04-04 | Davis Cup WG R1: USA vs RUS | RR | hard | Yevgeny Kafelnikov | 6-3 6-0 7-6(3) |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (173 vs 50). ATP, WTA & Challenger.