Anna Smashnova defeated Meghann Shaughnessy 1-6 7-5 6-3 in the Linz round of 32 on hard. The upset overturned the form book — Meghann Shaughnessy came in leading the head-to-head 5–2, but Anna Smashnova had been the form player, winning 3 of their last 7 on hard. Anna Smashnova narrowed the head-to-head to 5–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-08-21 | Forest Hills | F | hard | Meghann Shaughnessy | 1-6 6-0 6-4 |
| 2005-06-13 | s Hertogenbosch | R32 | grass | Meghann Shaughnessy | 6-2 6-4 |
| 2002-03-06 | Indian Wells | R16 | hard | Anna Smashnova | 4-6 6-3 6-1 |
| 2001-01-29 | Tokyo | R32 | hard | Meghann Shaughnessy | 6-2 6-1 |
| 2000-04-03 | West Palm 75K | SF | clay | Meghann Shaughnessy | 6-4 7-6(7) |
| 2000-01-03 | Auckland | QF | hard | Meghann Shaughnessy | 6-4 6-2 |
| 1998-09-28 | Santa Clara 75K | QF | hard | Anna Smashnova | 6-1 6-4 |
Averages over each player's completed matches in the selected window (26 vs 94). 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