On October 24, 2019, about 2100 central daylight time, a Cessna 172 airplane, N1443E, conducted a forced landing near Swea City, Iowa. The pilot, the sole occupant, received minor injuries, and the airplane sustained substantial damage. The airplane was registered to Iowaair, Inc, and operated by Iowa Flight Training, under the provisions of Title 14 Code of Federal Regulations Part 91 as a cross-country flight. Night visual meteorological conditions prevailed for the flight and no flight plan had been filed. The multi-leg flight originated from the Estherville Municipal Airport (EST), Estherville, Iowa, The pilot reported that he conducted a preflight inspection of the airplane. He added a half quart of oil to the engine from a bottle that was in the airplane. He also got another bottle of engine oil from the FBO (Fix Based Operator) to keep in the airplane. He disposed of the empty oil bottle and continued with his preflight. After engine start and before takeoff, he noted that both oil pressure and temperature gauges "seemed to read within the green range". While on the night cross-country flight, about half-way between Mason City and Fort Dodge, the pilot noticed that the oil pressure gauge indicated near zero, so he diverted back to EST. Shortly afterwards, the engine started to shake and then stopped producing full power. The airplane was unable to hold altitude, so he elected to conduct a forced landing to a road. An examination of the airplane by the responding Federal Aviation Administration (FAA) inspector found the airplane had impacted a dirt road and came to rest upright, in the ditch. Substantial damage was noted to the airplane's fuselage. The inspector also noted engine oil on the side of the cowling, and the engine's oil dipstick was on the ground, about 2 to 3 ft in front of the airplane. In a follow-up interview with the pilot, the FAA inspector reported the pilot would typically place the oil dipstick in the wing's tie down loop, when he checked or added oil to the engine. After the airplane was recovered to a hangar, an engine examination was conducted by maintenance personnel under the supervision of the FAA. Oil was observed on the firewall and the airplane's right-side fuselage. The oil filter was cut open and the engine borescoped; scoring on the number two and four cylinders was observed.