Philip Gubenco defeated Rob Steckley 6-1 3-6 7-6 in the Canada F2 round of 32 on hard. The upset overturned the form book — Rob Steckley came in leading the head-to-head 2–1, but Philip Gubenco had been the form player, winning 2 of their last 4 on hard. Philip Gubenco 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 |
| 2005-06-27 | USA F15 | SF | clay | Rob Steckley | 6-1 7-6(4) |
| 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.