Rob Steckley defeated Philip Gubenco 6-1 7-6 in the USA F15 semi-final on clay. The upset overturned the form book — Philip Gubenco came in leading the head-to-head 2–1. Rob Steckley narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-03-20 | Canada F3 | R32 | hard | Philip Gubenco | 6-2 1-6 6-2 |
| 2006-03-13 | Canada F2 | R32 | hard | Philip Gubenco | 6-1 3-6 7-6(5) |
| 2005-05-02 | Venezuela 1 Satellite 3 | R16 | hard | Rob Steckley | 6-2 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.