Darby Hendrickson was drafted by Toronto in 1990. Before actually joining the Leafs, however, he finished high school and spent two years at the University of Minnesota. He left college to spend most of 1993-94 with the U.S. National Team and to compete in the 1994 Olympic Winter Games. He then joined the Toronto organization, appearing in eight regular season games for St. John's and two playoff contests for the Leafs. In 1994-95,
In 1994-95 Hendrickson spent most of his season with the St. John's Maple Leafs but did tally his first NHL point during one of his eight appearances with Toronto. The following season, he played 46 games for the Leafs before being sent to the New York Islanders as part of a multi-player deal in March. He finished the season with the Islanders and then joined Team USA in the World Championships. In October 1996 it was back to Toronto for a draft pick, and Hendrickson notched points in 64 games.
That spring, he again participated in the World Championships. In 1997-98, he played a full 80 games for Toronto. The next season, he was back in a Leafs sweater for 35 games before being traded to Vancouver. After representing his homeland yet again at the 1999 World Championships, Hendrickson was back with the Canucks for 40 games and also played 20 games for the Syracuse Crunch. Prior to being selected by the Minnesota Wild in the 2000 Expansion Draft, the former Minnesota High School Player-of-the-Year played in his fifth World Championship in 2000. During the club's inaugural season, Hendrickson achieved a career high 29-point sin 72 games and quickly became one of the team's most popular players.
Following parts of four seasons with the Wild, Hendrickson who spent some time with the team's AHL affiliate in Houston during the 2003-04 season, and was acquired by the Colorado Avalanche in the latter stages of the season.
