Emin Agaev defeated Michael Jessup 6-7 6-4 6-3 in the USA 3 Masters 4 qualifying round on hard. The upset overturned the form book — Michael Jessup came in leading the head-to-head 2–0. Emin Agaev claimed a first win over Michael Jessup in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-24 | USA F5 | R32 | clay | Michael Jessup | 7-6 7-6 |
| 1998-09-11 | USA 3 Masters 2 | R32 | hard | Michael Jessup | 6-1 2-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.