Sherwood was selected in the seventh-round, 99th overall, by the
Youngstown Phantoms in the 2012 USHL entry draft. While Sherwood and his brother went undrafted to the NHL, they were both invited to the
Columbus Blue Jackets 2015 development camp. Leaving without a contract, Sherwood began his freshman season at
Miami University. Sherwood made the Ducks' 2018 opening night roster out of training camp. He made his NHL debut on October 4, where he recorded his first career NHL point to help the Ducks beat the
San Jose Sharks 5–2. He recorded his first career NHL goal in a 5–3 loss to the
Dallas Stars on October 13.
Colorado Avalanche As an impending restricted free agent following the conclusion of his entry-level deal, Sherwood was not tendered a qualifying offer by the Ducks and was released to free agency on October 9, 2020. He was soon signed on the opening day of free agency to a one-year, two-way contract with the
Colorado Avalanche, who then re-signed him to another one-year, two-way deal on July 22, 2021.
Nashville Predators As a free agent again preceding the
2022–23 season, Sherwood was signed to a one-year, two-way contract with the
Nashville Predators on July 14, 2022.
Vancouver Canucks After playing in 68 games for the Predators and establishing himself as an NHL regular in the
2023–24 season, Sherwood signed a two-year, $3 million contract as a free agent with the
Vancouver Canucks on July 1, 2024. He achieved his first NHL
hat trick, which was a natural hat trick in a 3–1 win over the Avalanche on December 16, 2024. He scored the goals in each of the three periods, among them a
shorthanded tally in the second period. By the end of the game, the Canucks' thirtieth of the season, Sherwood had already surpassed his career-high single-season goal total. On October 30, 2025, he scored a hat trick against the
St. Louis Blues, scoring in each of the three periods to lead the Canucks to a 4–3 win in a shootout.
San Jose Sharks On January 19, 2026, Sherwood was traded to the
San Jose Sharks in exchange for
Cole Clayton and second-round picks in
2026 and
2027. He signed a five-year contract extension on March 4, 2026. ==Personal life==