Cunningham attended Central High School in Pageland, South Carolina. In 2009, he earned First-Team All-State honors. He helped Central reach the 2008 Class AA state finals and a 14-1 record playing both tight end and defensive end. Cunningham collected 20 sacks in his senior year, but was deemed to be a better tight end prospect, mostly due to his blocking skills. Cunningham also excelled in basketball. He chose South Carolina over Michigan State and North Carolina State.