Jaan Frederik Brunken defeated Marius Zay 6-3 7-6 in the Germany F6 round of 16 on clay. The upset overturned the form book — Marius Zay came in leading the head-to-head 2–0. Jaan Frederik Brunken claimed a first win over Marius Zay in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-22 | Germany F7 | R32 | clay | Marius Zay | 6-1 6-4 |
| 2007-09-17 | Germany F17 | R16 | clay | Marius Zay | 6-2 6-1 |