

Maria Sakkari defeated Jessica Pegula 7-6 7-6 in the Fort Worth Finals round robin on hard. The upset overturned the form book — Jessica Pegula came in ranked #3, leading the head-to-head 7–4. Maria Sakkari narrowed the head-to-head to 7–5.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2025-07-27 | Montreal | R64 | hard | Jessica Pegula | 7-5 6-4 |
| 2025-01-06 | Adelaide | R16 | hard | Jessica Pegula | 6-4 6-1 |
| 2023-10-30 | Cancun Finals | RR | hard | Jessica Pegula | 6-3 6-2 |
| 2023-09-25 | Tokyo | SF | hard | Jessica Pegula | 6-2 6-3 |
| 2023-07-31 | Washington | SF | hard | Maria Sakkari | 6-3 4-6 6-2 |
| 2023-02-13 | Doha | SF | hard | Jessica Pegula | 6-2 4-6 6-1 |
| 2022-10-17 | Guadalajara 2 | F | hard | Jessica Pegula | 6-2 6-3 |
| 2022-02-21 | Doha | R16 | hard | Maria Sakkari | 6-4 7-5 |
| 2022-01-17 | Australian Open | R16 | hard | Jessica Pegula | 7-6 6-3 |
| 2021-03-22 | Miami | R16 | hard | Maria Sakkari | 6-4 2-6 7-6 |
| 2019-06-24 | Eastbourne | R64 | grass | Maria Sakkari | 6-2 6-1 |
Averages over each player's completed matches in the selected window (200 vs 200). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Sakkari M.: 3 days rest · 4 matches, 75 games (7d) · Pegula J.: 15 days rest. Higher means fresher. About
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Per-surface Serve / Return Rating (0–100, percentile within the hard field, opponent-adjusted over 52 weeks). About