[4] In order to maintain his NCAA eligibility, Caggiula chose to instead play with the Stouffville Spirit of the Ontario Junior Hockey League (OJHL).
[4] Due to his success at the junior level, Caggiula was drafted by the Des Moines Buccaneers of the United States Hockey League.
During this time, Caggiula verbally accepted a full scholarship offer to play college hockey for the University of North Dakota of the NCAA.
[7] Upon returning to the Spirit for a second season, Caggiula helped push them through a long playoff berth by tallying 17 goals and 37 points en route to their first-ever OJHL title.
[9] In his freshman year at North Dakota, Caggiula played in 39 games and ranked second among the team's rookies in points, goals, and assists.
[10] Prior to his junior year at North Dakota, Caggiula was invited and participated in the Buffalo Sabres 2014 Development camp.
[23] On December 30, 2018, Caggiula was traded by the Oilers along with Jason Garrison to the Chicago Blackhawks in exchange for Brandon Manning and Robin Norell.
[30] After a single season within the Penguins organization, Caggiula left as a free agent and opted to return to his original club, the Edmonton Oilers, after securing a two-year, two-way contract on July 1, 2023.