On December 3, 2017, about 1527 eastern standard time, a Cessna 180, N399F, was substantially damaged while landing at the Frederick Municipal Airport (FDK), Frederick, Maryland. The pilot and the two passengers were not injured, but the pilot-rated passenger sustained minor injuries. The airplane was registered to and operated by the pilot. Visual meteorological conditions prevailed for the personal flight conducted under the provisions of Title 14 Code of Federal Regulations Part 91. No flight plan was filed for the flight that departed Massey Aerodrome (MD1), Massey, Delaware, about 1445.The pilot stated that after a "smooth normal touchdown", the left tire failed. The left wheel rim dug into the runway pavement and the left wingtip struck the runway. The tail of the airplane also came up and the propeller blades struck the ground. The airplane came to rest on its nose just right of the runway centerline. A witness stated that the tailwheel-equipped airplane made a "shallow" bounce when it first touched down on runway 30. When the airplane touched down again, the left main tire blew. The airplane's left wing then dipped down and dragged on the runway surface for about 20-30 ft before the airplane went up on its nose and came to a rest. Postaccident examination of the airplane revealed the firewall and an engine mount were substantially damaged. The propeller, the spinner, the left main tire, and the left-wing tip were also damaged. The left tire assembly was examined by a National Transportation Safety Board Materials Specialist. The examination revealed features consistent with a progressive fracture through the rubber due to an overload failure of the underlying cords along one of the bias directions. There was no evidence of any preexisting damage or material deficiencies. The pilot held a private pilot certificate with a rating for airplane single-engine land. His last Federal Aviation Administration (FAA) Basic Med medical certificate was issued on May 3, 2017. The pilot reported a total of 1,850 flight hours, of which, 100 hours were in the accident airplane. At 1525, the weather at FDK was reported as wind from 330° at 5 knots, visibility 10 miles, and clear skies.