Luis Manuel Flores defeated Kevin Anderson 7-6 4-6 7-6 in the USA F27 round of 16 on hard. The upset overturned the form book — Kevin Anderson came in leading the head-to-head 1–0. Luis Manuel Flores claimed a first win over Kevin Anderson in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2007-08-18 | New Haven | Q32 | hard | Kevin Anderson | 6-4 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.