Wade Mcguire defeated Chris Rae 6-4 6-1 in the USA F13 round of 16 on hard. The upset overturned the form book — Chris Rae came in leading the head-to-head 1–0. Wade Mcguire claimed a first win over Chris Rae in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-19 | USA F11 | R32 | hard | Chris Rae | 6-1 6-3 |