Agustin Calleri defeated James Blake 6-4 6-2 in the Madrid Masters round of 64 on clay. The upset overturned the form book — James Blake came in leading the head-to-head 3–0. Agustin Calleri claimed a first win over James Blake in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-04-14 | Houston | QF | clay | James Blake | 6-4 6-3 |
| 2007-08-19 | New Haven | R16 | hard | James Blake | 3-6 7-6(2) 6-1 |
| 2007-05-20 | Dusseldorf | RR | clay | James Blake | 2-6 6-3 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 (200 vs 200). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About