Kevin Kim defeated David Caldwell 6-3 4-6 6-3 in the Washington round of 64 on hard. The upset overturned the form book — David Caldwell came in leading the head-to-head 1–0. Kevin Kim claimed a first win over David Caldwell in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-08-21 | Long Island | Q64 | hard | David Caldwell | 6-2 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.