David Critchley defeated Emin Agaev 6-4 7-6 in the USA 5 Masters 4 round of 32 on hard. The upset overturned the form book — Emin Agaev came in leading the head-to-head 1–0. David Critchley claimed a first win over Emin Agaev in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-12-06 | USA F22 | R32 | hard | Emin Agaev | 6-3 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.