Career
Before playing in the NHL, Regula played one season with the Chicago Steel of the United States Hockey League (USHL) and three seasons with the London Knights of the Ontario Hockey League (OHL). He had a successful time with his teams. He helped the Steel when they went on a run in the playoffs. They defeated the Youngstown Phantoms and Dubuque Fighting Saints. They went on to defeat the Sioux City Musketeers three games to two in the Final to win the Clark Cup. With the Knights, he was named to the First All-Rookie Team and Third All-Star Team.
He was drafted 67th overall by Detroit Red Wings in the 2018 NHL entry draft. He never played a game for the Red Wings. On October 28, 2019, the Red Wings traded Regula to the Chicago Blackhawks in exchange for Brendan Perlini. On November 11, 2019, Regula signed a three-year, $897,500 entry-level contract to join the Blackhawks. He was sent down to play for their AHL-affiliate Rockford IceHogs.
On May 6, 2021, the Blackhawks called him up and Regula made his NHL debut in a 2–1 overtime win against the Carolina Hurricanes. On April 18, 2022, Regula scored his first NHL goal against Jacob Markström in a 5–2 loss against the Calgary Flames.
On June 26, 2023, the Blackhawks traded Regula along with Ian Mitchell to the Boston Bruins in exchange for Nick Foligno and Taylor Hall. On July 17, Regula signed a one-year, $875,000 contract to stay with the Bruins. On July 12, 2024, Regula signed a two-year contract to stay with the Bruins.
