Prior to turning professional, Pitlick played for the Muskegon Lumberjacks and Waterloo Black Hawks in the United States Hockey League (USHL).
[1] Pitlick began playing in the United States Hockey League (USHL) for the Waterloo Black Hawks.
After spending the 2014–15 season with the Black Hawks, he was traded to the Muskegon Lumberjacks in exchange for a first and tenth round pick in the USHL draft.
Pitlick was assigned to the Predators' American Hockey League (AHL) affiliate, the Milwaukee Admirals, for the 2019–20 season.
[22] He registered his first two NHL points, assisting on goals by Colton Sissons and Mikael Granlund in a 7–2 win over the Tampa Bay Lightning on April 13.
[17] After attending the Predators 2021 training camp, prior to being reassigned to the AHL to begin the 2021–22 season, Pitlick was claimed off waivers by the Minnesota Wild on October 6.
[25] In his fifth game with the Wild on November 13, Pitlick scored his first three NHL goals with a natural hat trick against goaltender Philipp Grubauer, securing a 4–2 win over the Seattle Kraken.
[28] He scored his first goal for the team in the next game on January 17, taking a pass from Jonathan Drouin to beat Karel Vejmelka of the Arizona Coyotes in a 7–2 loss.
[29] He made an immediate impact on arrival in Montreal, in the midst of what was a historically poor season for the team, registering six points in his first seven games and almost double the average ice time he had with the Wild.
[17] After initially testing free agency, Pitlick was re-signed to a two-year, $2.2 million contract extension with the Canadiens on July 16.
On November 7, with fellow forward Evgenii Dadonov scheduled to return to the roster from injured reserve, it was announced that Pitlick was being put on waivers.
[33][35] In a memorable game against the Toronto Maple Leafs on January 21, 2023, Pitlick scored in overtime in three-on-three play to win the match for Montreal.
[39] He made his debut on January 9 in a 2–1 loss to the Edmonton Oilers, playing on the first line with Philipp Kurashev and Taylor Raddysh.
[43] As an un-signed free agent well into the midpoint of the 2024–25 season, Pitlick was belatedly signed to a AHL contract with the San Jose Barracuda on February 5, 2025.