| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2012-08-19 | Winston-Salem | R32 | hard | Andy Roddick | 7-6(6) 7-6(6) |
| 2011-03-10 | Indian Wells Masters | R64 | hard | Andy Roddick | 6-3 7-5 |
| 2010-02-15 | Memphis | R32 | hard | Andy Roddick | 6-3 4-6 7-6(3) |
| 2009-06-08 | Queen's Club | SF | grass | James Blake | 4-4 RET |
| 2006-07-17 | Indianapolis | F | hard | James Blake | 4-6 6-4 7-6(5) |
| 2006-06-12 | Queen's Club | SF | grass | James Blake | 7-5 6-4 |
| 2003-08-11 | Cincinnati Masters | R16 | hard | Andy Roddick | 7-6(2) 6-2 |
| 2002-10-21 | Basel | R16 | hard | Andy Roddick | 7-6(6) 6-3 |
| 2002-04-22 | Houston | QF | clay | Andy Roddick | 6-2 6-4 |
| 2002-02-25 | San Jose | QF | hard | Andy Roddick | 6-4 6-2 |
| 2002-02-18 | Memphis | F | hard | Andy Roddick | 6-4 3-6 7-5 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.