Matias Boeker defeated Michael Jessup 6-3 7-5 in the USA F14 qualifying round on hard. The upset overturned the form book — Michael Jessup came in leading the head-to-head 2–0. Matias Boeker claimed a first win over Michael Jessup in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-31 | USA F6 | R32 | clay | Michael Jessup | 6-1 6-0 |
| 1999-05-17 | USA F4 | R64 | clay | Michael Jessup | 2-6 6-4 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.