Lleyton Hewitt defeated Andre Agassi 6-3 6-4 in the Masters Cup round robin on hard. The upset overturned the form book — Andre Agassi came in leading the head-to-head 4–3, defending last year's final. Lleyton Hewitt narrowed the head-to-head to 4–4.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-08-02 | Cincinnati Masters | F | hard | Andre Agassi | 6-3 3-6 6-2 |
| 2002-08-26 | US Open | SF | hard | Andre Agassi | 6-4 7-6(5) 6-7(1) 6-2 |
| 2002-08-05 | Cincinnati Masters | QF | hard | Lleyton Hewitt | 7-5 6-3 |
| 2002-02-25 | San Jose | F | hard | Lleyton Hewitt | 4-6 7-6(6) 7-6(4) |
| 2001-03-12 | Indian Wells Masters | SF | hard | Andre Agassi | 6-4 3-6 6-4 |
| 1999-07-26 | Los Angeles | QF | hard | Andre Agassi | 5-4 RET |
| 1998-01-05 | Adelaide | SF | hard | Lleyton Hewitt | 7-6(5) 7-6(4) |
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 (200 vs 200). ATP, WTA & Challenger.