Andy Roddick defeated Tim Henman 7-5 7-6 in the Masters Cup round robin on hard. The upset overturned the form book — Tim Henman came in leading the head-to-head 3–1, but Andy Roddick had been the form player, winning 3 of their last 4 on hard. Andy Roddick narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-03-08 | Indian Wells Masters | QF | hard | Tim Henman | 6-7(6) 7-6(1) 6-3 |
| 2003-10-27 | Paris Masters | SF | hard | Tim Henman | 7-6(4) 7-6(7) |
| 2003-08-25 | US Open | R128 | hard | Andy Roddick | 6-3 7-6(2) 6-3 |
| 2003-07-28 | Washington | SF | hard | Tim Henman | 1-6 6-3 7-6(1) |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.