Matej Pampoulov defeated Luben Pampoulov 4-6 6-2 6-4 in the Yugoslavia F6 qualifying round on clay. Matej Pampoulov extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-16 | Switzerland 2 Masters 1 | QF | carpet | Matej Pampoulov | 5-7 7-6 7-6 |
| 1999-10-16 | Switzerland 2 Masters 3 | SF | carpet | Luben Pampoulov | 6-3 3-6 6-4 |