Greenwater RCMP says it happened about nine kilometres west and six kilometres north of Archerwill shortly before 10 a.m.
Police believe weather conditions were a factor as there was extreme fog and frost at the time of takeoff.
Its initial investigation shows the two occupants were trapped inside the plane.
Tisdale Fire Department, Archerwill first responders, Rose Valley and Naicam EMS, the Shamrock Ambulance ACP Rover from Wadena and STARS air ambulance also attended the crash.
The two men, 58 and 52 years old, were removed from the plane and taken to hospital.
RCMP continue to investigate.