Jeroen Masson defeated Matwe Middelkoop 7-6 6-3 in the Netherlands F3 round of 16 on clay. The upset overturned the form book — Matwe Middelkoop came in leading the head-to-head 1–0. Jeroen Masson claimed a first win over Matwe Middelkoop in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2007-08-20 | Netherlands F4 | QF | clay | Matwe Middelkoop | 6-4 4-6 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.