In July 1993, the Athletics traded Henderson to the playoff-bound Toronto Blue Jays for Steve Karsay and José Herrera. He performed disappointingly for the Jays, hitting only .215 in 44 games, which was probably due to the fact that he fractured a bone on his hand early on with the team, after being hit by a pitch, although he still contributed 22 stolen bases and 37 runs scored. However, his hitting woes continued in the post-season, batting .120 in the American League Championship Series and .227 in the World Series. Nevertheless, Henderson was involved in the final play of the World Series that year in one fashion for which he was most known, as he and Paul Molitor scored on Joe Carter's Series-ending home run. After winning his second World Series ring with Toronto, he re-signed as a free agent with Oakland in December 1993.