Mikhail Vasiliev defeated Richard Ruckelshausen 7-6 6-2 in the Sudan F2 round of 32 on clay. The upset overturned the form book — Richard Ruckelshausen came in leading the head-to-head 1–0. Mikhail Vasiliev claimed a first win over Richard Ruckelshausen in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-15 | Italy F15 | R32 | clay | Richard Ruckelshausen | 6-3 6-4 |