On June 25, 2004, about 1045 mountain daylight time, a Maule M-7-235C, N1936P, registered to Dark Farm Inc. and flown by the pilot as a 14 CFR Part 91 personal flight, lost directional control during the landing roll at Frank Wiley Field, Miles City, Montana, which resulted in the left main landing gear failure. Visual meteorological conditions prevailed at the time and no flight plan was filed. The aircraft was substantially damaged and the private pilot and his passenger were not injured. The flight originated from Pierre, South Dakota, earlier that day. During a telephone interview and subsequent written statement, the pilot reported that during the landing roll on runway 30, the aircraft started to veer to the left. The pilot attempted corrective action with right rudder control however, he felt a vibration in the tailwheel like it was "skidding" as the aircraft continued to the left. The right main tire came loose from the rim and the left main landing gear failed at the fuselage attached points. During these actions, both wing tips contacted the runway surface. The aircraft came to rest with the left wing on the runway surface. Wing skin wrinkles were noted on the upper surface, and a rivet seam line was pulled apart on the lower surface. The left side step was pushed up into the floor board area, and the occupant seat structure was damaged. The right side wing tip was damaged as well as the outboard aileron tip. Inspection of the aircraft by a Federal Aviation Administration Inspector from the Helena, Montana, Flight Standards District Office, reported that the left side main wheel was flat with a small puncture hole noted on the outer rim. The right side main tire was also flat and the rim was damaged from side loading contact with the runway surface. The tailwheel was intact and free to rotate.