Artis Leon Ivey Jr. aka Coolio, who is best known for his 1995 single Gangsta's Paradise, was scheduled to perform in Toronto, Montreal, Quebec City and Ottawa.
But his manager, Blair "Goast" Bryson, said Canada Border Services Agency would not allow him to cross the border due to the charge.
Ivey Jr. paid a fine for the charge and performed community service, Bryson added, claiming the border problems are a new one for the rapper.
"He hasn't had a problem getting in anywhere else. Like I've taken him to the U.K., Australia, Russia, he hasn't had any problem getting into those countries. And I mean recent," said Bryson.
"He's been coming in and out of Canada for the past 15 years. Now this old charge is an issue, you guys never made a big deal about it before."
Ivey Jr. also faced a felony narcotics charge in 2009 stemming from an incident at the Los Angeles International Airport.
All ticket-holders will be given full refunds. Coolio is scheduled to perform in Russia next week.