Fredrik Loven defeated Simon Dickson 6-2 6-4 in the New Zealand F2 qualifying round on hard. The upset overturned the form book — Simon Dickson came in leading the head-to-head 1–0, but Fredrik Loven had been the form player, winning 3 of their last 7 on hard. Fredrik Loven claimed a first win over Simon Dickson in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-11 | Great Britain F11 | R32 | hard | Simon Dickson | 6-3 3-6 6-3 |