Junior Growing up in Pickering, Caggiula played minor midget hockey with the Ajax/Pickering Raiders in 2009–10 before being drafted in the third round of the
Ontario Hockey League (OHL) by the
Erie Otters. At the time of the draft, Caggiula had finished the season with 95 points through 66 games. In order to maintain his NCAA eligibility, Caggiula chose to instead play with the
Stouffville Spirit of the
Ontario Junior Hockey League (OJHL). As a rookie in the OJHL, Caggiula was selected for the OJHL North-West Conference 1st Team All-Prospect after tallying 45 points in 48 games. He attended the Buccaneers USHL Fall Classic event before returning to the Spirit for another season. During this time, Caggiula verbally accepted a full scholarship offer to play
college hockey for the
University of North Dakota of the
NCAA. 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.
Collegiate Caggiula played for the Fighting Sioux at the University of North Dakota from 2012 to 2016 while majoring in
kinesiology. 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. Prior to his junior year at North Dakota, Caggiula was invited and participated in the
Buffalo Sabres 2014 Development camp. He began his junior season strong by averaging 1.44 points per game during November for 13 points through nine games. His point total led the conference and was tied for third nationally. At the conclusion of his junior year, Caggiula was named to the
NCHC Second All-Star Team. In his senior season with North Dakota in
2015–16, Caggiula led North Dakota to win the
2016 NCAA championship and was named Most Outstanding Player of the tournament. He was also named to the
Second-Team All-American West and to the
NCHC First All-Star Team. Following the end of the season, Caggiula gained attention from numerous NHL teams as the top available collegiate free agent. On May 7, 2016, Caggiula agreed to a two-year entry-level deal with the
Edmonton Oilers.
Professional Although Caggiula was expected to make his debut on October 12, it was delayed due to an injury. His debut eventually came on November 19 in a 5–2 win over the
Dallas Stars. Caggiula scored his first NHL goal on December 3, 2016 in an Oilers overtime win over the Anaheim Ducks. On June 14, 2018, Caggiula re-signed with the Oilers on a two-year contract. During the
2018–19 season, Caggiula suffered a hand injury during a game against the
St. Louis Blues and was placed on injured reserve. At the time of the injury, Caggiula had recorded 10 points in 23 games. 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. On February 1, 2019, Caggiula scored his first goal as a Blackhawk in a 7–3 win against the
Buffalo Sabres. Despite hampered by injury in the
2019–20 season, Caggiula was a dependable role player with the Blackhawks, posting 9 goals and 15 points in 40 regular season games, before the season was effectively cut short due to the
COVID-19 pandemic. Due to salary cap constraints, Caggilua as an impending restricted free agent was not tendered a qualifying offer by Blackhawks, ending his two-year tenure and releasing him to free agency on October 8, 2020. On December 21, 2020, Caggiula was signed to a one-year, $700,000 contract with the
Arizona Coyotes. In the pandemic delayed
2020–21 season, Caggiula appeared in 27 regular season contests, posting 1 goal and 7 points, before he was placed on waivers by Arizona on April 8, 2021, and was subsequently claimed by the
Buffalo Sabres the following day. On July 27, 2021, Caggiula signed a one-year, $750,000 extension with the Sabres. As a free agent from the Sabres, on July 13, 2022, Caggiula signed to a one-year, two-way contract with the
Pittsburgh Penguins. 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.
Switzerland On June 2, 2025, Caggiula signed a one-year contract to play for
Lausanne HC in Switzerland's
National League. ==Personal life==