James Blake defeated Agustin Calleri 3-6 7-6 6-1 in the New Haven round of 16 on hard. The result followed the form book — James Blake came in leading the head-to-head 2–1, defending last year's round of 32. James Blake extended 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 |
| 2007-05-20 | Dusseldorf | RR | clay | James Blake | 2-6 6-3 6-4 |
| 2002-10-14 | Madrid Masters | R64 | clay | Agustin Calleri | 6-4 6-2 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.