Donavan September defeated Andrew Anderson 6-4 6-4 in the Philippines F1 round of 32 on hard. The result followed the form book — Donavan September came in leading the head-to-head 2–0. Donavan September extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-16 | South Africa Masters 3 | R16 | hard | Donavan September | 7-5 6-3 |
| 1999-10-16 | South Africa Masters 4 | R32 | hard | Donavan September | 6-0 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.