| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2012-01-16 | Australian Open | R64 | hard | Lleyton Hewitt | 3-6 6-3 6-4 RET |
| 2009-06-22 | Wimbledon | QF | grass | Andy Roddick | 6-3 6-7(10) 7-6(1) 4-6 6-4 |
| 2009-06-08 | Queen's Club | R16 | grass | Andy Roddick | 7-6(2) 7-6(4) |
| 2009-02-16 | Memphis | SF | hard | Andy Roddick | 2-6 7-6(4) 6-4 |
| 2006-08-28 | US Open | QF | hard | Andy Roddick | 6-3 7-5 6-4 |
| 2005-08-15 | Cincinnati Masters | SF | hard | Andy Roddick | 6-4 7-6(4) |
| 2005-03-07 | Indian Wells Masters | SF | hard | Lleyton Hewitt | 7-6(2) 6-7(3) 7-6(4) |
| 2005-01-17 | Australian Open | SF | hard | Lleyton Hewitt | 3-6 7-6(3) 7-6(4) 6-1 |
| 2004-11-15 | Masters Cup | SF | hard | Lleyton Hewitt | 6-3 6-2 |
| 2004-06-07 | Queen's Club | SF | grass | Andy Roddick | 7-6(7) 6-3 |
| 2001-08-27 | US Open | QF | hard | Lleyton Hewitt | 6-7(5) 6-3 6-4 3-6 6-4 |
| 2001-05-28 | Roland Garros | R32 | clay | Lleyton Hewitt | 6-7(6) 6-4 2-2 RET |
| 2001-03-19 | Miami Masters | QF | hard | Lleyton Hewitt | 6-3 6-2 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.