Ai Sugiyama defeated Mary Pierce 6-2 6-4 in the Rome round of 32 on clay. The upset overturned the form book — Mary Pierce came in leading the head-to-head 6–5. Ai Sugiyama narrowed the head-to-head to 6–6.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-10-23 | Linz | R32 | hard | Mary Pierce | 7-6(3) 7-6(5) |
| 2005-08-01 | San Diego | F | hard | Mary Pierce | 6-0 6-3 |
| 2002-06-17 | Eastbourne | R32 | grass | Ai Sugiyama | 6-4 6-4 |
| 2002-04-01 | Sarasota | R32 | clay | Mary Pierce | 6-3 6-3 |
| 2000-01-17 | Australian Open | R16 | hard | Ai Sugiyama | 7-5 6-4 |
| 1999-10-18 | Kremlin Cup | R16 | carpet | Ai Sugiyama | 6-4 3-6 6-3 |
| 1999-08-09 | Manhattan Beach | R16 | hard | Mary Pierce | 6-2 7-5 |
| 1999-08-02 | San Diego | R32 | hard | Ai Sugiyama | 6-3 4-6 6-1 |
| 1998-10-26 | Luxembourg | QF | hard | Mary Pierce | 6-3 6-2 |
| 1998-10-20 | Kremlin Cup | R32 | carpet | Mary Pierce | 5-7 6-2 6-4 |
| 1997-03-01 | Fed Cup WG1 QF: JPN vs FRA | RR | hard | Ai Sugiyama | 7-5 6-7(7) 6-4 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (160 vs 52). ATP, WTA & Challenger.