Jennings was a four year letter winner at Illinois College in the sport of football. Jennings played wide receiver for the Blueboys and had a remarkable career during his time at IC. He was a team captain, All-Conference, All-American, and team MVP. He was awarded the William J. Downer Award for most outstanding male student-athlete in 2009 and 2010. He is the current school record holder for single game, single season, and career receptions, receiving yards, and receiving touchdowns.