Tragedy struck the Western Hills High School football team twice in 2014. Less than a week before their first game, Dillon Walker, a Western Hills student that graduated the previous June, passed away August 16, 2014. While not a football player himself, he was very close to several players on the team. Then during the season, Garrett Hodapp, a freshman on the team (#32), committed suicide October 7, 2014.

Despite these tragedies, perhaps fueled by them, the team had more success in 2014 than the past two seasons combined. After winning only one game each of the past two seasons and missing the playoffs, the Wolverines went 5-5 in 2014, winning the last game of the regular season, which clinched a playoff berth for the first time since 2011. They would go on to lose that game to Russell High School 37-16.