The first incident happened just before 12:43 a.m.  near the corner of Sherway Drive and The West Mall in Etobicoke.
Police said they were called to the area for the sound of gunshots and arrived to find a man suffering from a single gunshot wound.
He was taken to hospital in non-life threatening condition.
More than three hours later, police said they were called to the corner of Morningside and Sheppard avenues in Scarborough for a shooting.
Shortly after 3:03 a.m., a man with at least one gunshot wound showed up at the hospital.
Investigators say a number of vehicles were seen speeding away from the intersection before police arrived.