Michael Jessup defeated Matias Boeker 2-6 6-4 6-2 in the USA F4 round of 64 on clay. Michael Jessup extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-06-09 | USA F14 | QF | hard | Matias Boeker | 6-3 7-5 |
| 1999-05-31 | USA F6 | R32 | clay | Michael Jessup | 6-1 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.