Chris Rae defeated Wade Mcguire 6-1 6-3 in the USA F11 round of 32 on hard. The upset overturned the form book — Wade Mcguire came in leading the head-to-head 1–0. Chris Rae claimed a first win over Wade Mcguire in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-02 | USA F13 | R16 | hard | Wade Mcguire | 6-4 6-1 |