Highlands defeated Ohio Division II power Trotwood-Madison 24-20 to win the last game of the 2007 Kirk Herbstreit Ohio vs. USA Challenge III, played at the University of Cincinnati's Nippert Stadium. This was a significant win for the 'Birds, since Trotwood-Madison has several NCAA Division I-A recruits, including a quarterback many consider to be the best QB in the entire state of Ohio. Also, the "Herbie" is the most notable high school football event in the entire country. Highlands won the game on the strength of its powerful running game, as the Bluebirds amassed 313 total yards in the game. The highlight play of the game was backup quarterback Tony Guidugli's 51-yard TD pass to RB Josh Conner to take the lead once and for all. Highlands' 2007 varsity record to-date: 2-0.
Also this week, the Highlands freshman squad defeated archrival Covington Catholic 7-6 in overtime to begin the freshman season 1-0, while the Highlands JV team lost to Cincinnati Withrow 42-26 to go to 1-1 on the JV season.