On May 9, 2018, Cleveland traded Urshela to the Toronto Blue Jays for cash considerations or a player to be named later. Urshela batted .233 with one home run and three RBIs in 19 games for Toronto, before he was designated for assignment by the Blue Jays on June 26. He cleared waivers and was assigned outright to the Triple-A Buffalo Bisons on July 3. He batted .244 in 91 plate appearances for the Bisons.
On August 4, 2018, the Blue Jays traded Urshela to the New York Yankees in exchange for cash considerations. The Yankees assigned him to the Scranton/Wilkes-Barre RailRiders. He worked with Phil Plantier, the RailRiders' hitting coach, to make changes to his batting stance. Urshela batted .307 in 107 plate appearances for Scranton/Wilkes-Barre.