Although he was now eligible for American Hockey League (AHL) assignment, San Jose chose to leave him unsigned, knowing he still had room to improve in the OHL.

For development, Cheechoo joined San Jose's AHL affiliate, the Kentucky Thoroughblades, in the 2000–01 season before deciding to give the NHL another try and retaining hockey agent Thayne Campbell.

In 2002–03, after scoring seven points (three goals and four assists) in nine games with the Cleveland Barons (the relocated Kentucky Thoroughblades franchise), Cheechoo was recalled to San Jose to help revitalize the struggling team.

[1] Much of Cheechoo's success was augmented by the Sharks acquisition of his new linemate, superstar center Joe Thornton in late November.

[3][4] In the 2006–07 season, Cheechoo got off to a slow start as he, Joe Thornton and newly acquired power forward Mark Bell failed to click.

However, after a struggling Bell was demoted to the press box in favour of young speedster Milan Michalek, Cheechoo picked it up, finishing the season with 37 goals and 69 points in 76 games.

During the 2007 off-season, Cheechoo required double hernia surgery to repair injuries he suffered during the Sharks' playoff run.

[8] Cheechoo, who was heading into the final year of a five-year contract signed with San Jose in 2006, was reportedly owed $3.5 million for the 2010–11 season.

[11] He was released from the tryout 22 days later, on September 26, following his appearance in two pre-season games where he failed to register a point and posted a −2 rating.

Despite his efforts, Dallas felt Cheechoo could not out perform their current players and therefore released him so he would have the opportunity to join another team.

While playing with the Blues' AHL affiliate, the Peoria Rivermen, Cheechoo earned his 500th career professional point on November 27 against the Chicago Wolves.

[14] A free agent upon the 2012–13 NHL lockout, Cheechoo was belatedly signed to a professional try-out contract with the Oklahoma City Barons of the AHL during the midpoint of the 2012–13 season on January 20, 2013.

[15] On July 10, 2013, Cheechoo left North America and signed a one-year contract with Croatian club, Medveščak Zagreb of the Kontinental Hockey League (KHL).

He was recognized at the SAP Center in San Jose prior to the Sharks' game against the Calgary Flames on March 24, 2018.