Philip Gubenco defeated Nicolas Todero 6-2 6-4 in the USA F29 round of 32 on hard. The upset overturned the form book — Nicolas Todero came in leading the head-to-head 3–1. Philip Gubenco narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-10-13 | USA F28 | R16 | hard | Nicolas Todero | 6-1 6-3 |
| 2001-04-09 | USA F9 | R32 | hard | Nicolas Todero | 4-6 7-6(2) 6-4 |
| 2000-11-13 | USA F27 | R32 | hard | Philip Gubenco | 6-4 6-4 |
| 2000-06-26 | Canada F3 | R16 | hard | Nicolas Todero | 6-4 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.