The two cars collided just after 6 p.m. and struck the pole on Dufferin Street between Steeles Avenue West and Glen Shields Avenue, police said in a statement.
The two cyclists were riding by when that happened.
One cyclist was killed when the pole fell, and the other seriously injured.
Two people in one of the cars were transported to hospital with minor injuries.
One person in the other vehicle was taken to hospital with minor injuries.