Michael Jessup defeated Emin Agaev 7-6 7-6 in the USA F5 round of 32 on clay. Michael Jessup extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-09-11 | USA 3 Masters 2 | R32 | hard | Michael Jessup | 6-1 2-6 6-3 |
| 1998-09-11 | USA 3 Masters 4 | QF | hard | Emin Agaev | 6-7 6-4 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.