Defilippis attended high school at Benedictine in Savannah, Georgia. In Defilippis senior year he threw for over 700 yards and rushed for over 800 yards and as the team's quarterback. Also acting as the team's punter, he averaged 37 yards per punt. His performance would help lead his team to the Georgia 3-AAA state playoffs. Defilippis also played basketball and baseball all four years in high school.
Defilippis signed a scholarship to Savannah State University. As a true freshman, Defilippis would see action in four games, completing one pass for 40 yards. In his sophomore year, Defilippis saw action in seven games for the SSU, completing 56.1% of his passes for a total of 425 yards and throwing 3 touchdowns. His best game came on Sept. 26, 2009 against Concordia Selma, when he rushed for 41 yards off of five attempts and competed 9 of 12 passes for a total of 95 yards and two touchdowns. In his junior and final year at Savannah State, Defillippis played in ten games for the Tigers and completed 44.2 of his passes (50-113) for 457 yards. He threw for two touchdowns, averaged 45.7 passing yards per game, and had 61 rushing yards on the season. He also had three punts for 75 yards including a 33-yard punt against N.C. Central. Defilippis' best game came against Albany State, as he had a season-high 15 completions for 153 and a season-high 39 yard completion came in that same game.