DePaola was born in Sparks, Maryland, a town in Baltimore County. In 2001, DePaola entered Hereford High School in Parkton, Maryland as a freshman with a passion for baseball, but soon shifted his focus to football. Depaola quickly became an integral part of the school’s football team, the Bulls, and was promoted to the varsity squad his sophomore year. That same year, DePaola helped the Bulls win the 2A state championship in football. DePaola’s success continued into his senior year, in which he again lead the football team to the state championship but ultimately lost. As the team’s quarterback, DePaola completed his senior year completing 68% of his passes, throwing 22 touchdowns, 2,092 passing yards, and allowing only 7 interceptions, leading his team to set a state record for single season scoring of 636 points. In addition to receiving the Baltimore County Offensive Player of the Year award from The Baltimore Sun, DePaola also received honors as an all-Metro and All-State player. The last football game DePaola would play during his high school career would be the Good Samaritan Bowl hosted at the Navy–Marine Corps Memorial Stadium in Annapolis, Maryland. While DePaola did make football his athletic focus during his high school career, he continued to play baseball earning all-Metro honors his senior year after batting.527 and posting a 3-1 record as a pitcher. After high school, DePaola went on to Rutgers University and joined the football team as a walk-on. His first year, DePaola was redshirted, a technique in player management for college sports in which students may practice with the team while attending classes, but not play in any games. During his first two seasons on the team, including his redshirt season, DePaola served as the team's third string quarterback, helping the team prepare for games during practices. DePaola served as the team's holder on field goals during his third season, not once dropping the ball. It was during this season when DePaola was featured on ESPN SportsCenter for a play in which DePaola received the ball for a field goal against the University of South Florida, but instead completed a fifteen-yard pass for a touchdown. DePaola began his fourth season with Rutgers as a wide receiver, but became the team's long snapper when the starting long snapper Jeremy Branch sustained a leg injury. During the final four games of that season and for the entirety of his fifth season, DePaola served as the teams starting long snapper, playing in every game that final season. DePaola went undrafted by a professional team after completing college.
Although DePaola was not drafted after college, he did sign with the Tampa Bay Buccaneers as a long snapper in early August 2012 during training camp, but after three weeks he was waived on August 27, 2012. On Thursday January 3, 2013, DePaola was signed to a future contract by the Tampa Bay Buccaneers, meaning that at the start of the upcoming season DePaola would sign with the Buccaneers and be added to the active roster. DePaola was one of the final cuts in training camp in favor of long snapper Andrew Economos. On May 14, 2014, DePaola re-signed with the Buccaneers under a two-year contract. DePaola made his on-field debut against the Carolina Panthers on September 7, 2014, with two snaps on successful extra point attempts and one tackle assist. He went on to be the long snapper for the Buccaneers for three seasons from 2014 to 2016. On August 22, 2017, DePaola re-signed with the Buccaneers, only to be released on September 1, 2017 during final roster cuts.
On March 16, 2018, DePaola signed a four-year contract with the Oakland Raiders. In Week 1, DePaola suffered a torn ACL and was placed on injured reserve on September 12, 2018. On August 25, 2019, DePaola was released by the Raiders.
Carolina Panthers
On August 28, 2019, DePaola was signed by the Carolina Panthers. He was released during final roster cuts on August 30, 2019.