Emin Agaev defeated Brandon Kramer 7-5 6-1 in the USA F22 round of 64 on hard. The upset overturned the form book — Brandon Kramer came in leading the head-to-head 1–0, but Emin Agaev had been the form player, winning 2 of their last 5 on hard. Emin Agaev claimed a first win over Brandon Kramer in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-10 | USA 2 Masters 4 | R32 | hard | Brandon Kramer | 6-3 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.