On September 9, 2022, about 1845 eastern daylight time, an Engineering & Research 415-C airplane, N99209, was substantially damaged when it was involved in an accident near Galion, Ohio. The student pilot was not injured. The airplane was operated as a Title 14 Code of Federal Regulations Part 91 personal flight. The student pilot stated that before departure he performed an engine run-up that included a check of the magnetos and carburetor heat, noting normal rpm decrease for each. He initiated the takeoff noting full rpm during the takeoff roll and the airplane became airborne about the usual location along the length of the runway. On the upwind leg of the airport traffic pattern when the airplane was about 300 ft above ground level, the engine began to lose power. The pilot lowered the airplane’s nose to maintain 65 knots then made a left turn to return to the airport. When the airplane was close to the airport the engine experienced a total loss of power and the student pilot realized that the airplane was too high to land on the runway. He flew over and then north of the airport where he intended to land on an east/west oriented road. The airplane subsequently impacted a powerline pole and came to rest on the road. Postaccident examination of the airplane following recovery revealed structural damage to the fuselage and aft empennage. Examination of the engine revealed the exhaust valve of the No. 2 cylinder was stuck open. Review of the engine maintenance records revealed that a reconditioned cylinder was installed at the No. 2 position in March 1990. About 6 ½ years and 79 hours later, the No. 2 cylinder was removed and the valves were ground. Although the engine was overhauled in January 1998, the only work done to the cylinders were that they were honed, and the valves were ground and lapped. Since the engine overhaul, the No. 2 cylinder was removed in 2005 and again in 2009. The entry in 2005 specified “stuck valves” while the reason for the valve removal in 2009 was not noted. Both entries specified cleaning and/or reaming of the valve guides. In September 2019, which was before the pilot owned the airplane, a “stuck open” exhaust valve of the No. 2 cylinder was reported, with a corrective action of reaming the guide and polishing the valve stem. The engine had accrued about 63 hours and nearly 3 years since the last exhaust valve incident was logged and over 32 years and about 628 hours since the reconditioned cylinder was installed on the engine. According to the engine manufacturer Standard Practice Maintenance Manual, the expected repair for an engine experiencing a stuck valve included cleaning of the parts of the cylinder and dimensional checks of the components. The manual did not have any guidance for a repetitive issue.