Angela Haynes defeated Rossana De Los Rios 6-3 6-4 in the Philadelphia q32 on carpet. The upset overturned the form book — Rossana De Los Rios came in leading the head-to-head 5–3, defending last year's round of 16. Angela Haynes narrowed the head-to-head to 5–4.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-08-04 | Monterrey 100K | R16 | hard | Angela Haynes | 4-6 7-6(5) 6-3 |
| 2008-03-31 | Pelham AL 25K | QF | clay | Rossana De Los Rios | 4-6 6-0 6-1 |
| 2007-10-08 | San Francisco CA 50K | QF | hard | Angela Haynes | 0-6 6-4 6-4 |
| 2006-11-13 | Lawrenceville GA 50K | R16 | hard | Rossana De Los Rios | 6-1 6-3 |
| 2006-05-15 | Palm Beach Gardens 25K | SF | clay | Rossana De Los Rios | 6-4 6-3 |
| 2004-10-11 | Ashburn VA 50K | QF | hard | Rossana De Los Rios | 5-7 6-1 6-3 |
| 2004-07-05 | College Park MD 25K | SF | hard | Rossana De Los Rios | 3-6 6-3 6-3 |
| 2004-05-10 | Charlottesville VA 50K | R32 | clay | Angela Haynes | 6-3 6-2 |
Averages over each player's completed matches in the selected window (16 vs 44). ATP, WTA & Challenger.
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About