At about 3 a.m., paramedics were called to reports of shots fired outside the C Lounge nightclub at 456 Wellington St., just west of Spadina.
The woman, believed to be in her 20s, was shot once and died in hospital.
The man was hit five or six times and is being treated in hospital. He was found at the scene conscious and breathing.
The victims were found in two locations. The man was outside the Shell gas station at Spadina, the woman was across the street.
Names and ages of the victims have not been released. Police have not released any information about suspects.
Wellington Street near Draper Street is closed in both directions while police investigate.