On September 25, 2019, at 1335 central daylight time, a Lancair 320 airplane, N52WL, experience a landing gear system malfunction while on approach to Bolivar Municipal Airport (M17), Bolivar, Missouri. The private pilot was not injured, and the airplane sustained substantial damage to the right wing during the landing. The airplane was registered to and operated by the pilot as a Title 14 Code of Federal Regulations Part 91 personal flight. Visual meteorological conditions prevailed at the time of the accident, and a flight plan had not been filed. The airplane departed the Sparta/Fort McCoy Airport, Sparta, Wisconsin, at 1115, and was destined for M17. According to the pilot, while on visual approach to M17, he activated the landing gear extension switch and noticed the right main landing gear indication was not illuminated. The pilot recycled the landing gear, checked the landing gear circuit breaker, and performed an emergency landing gear extension; however, the right main landing gear did not extend. The pilot burned fuel for about 1 hour and landed on runway 18. During the landing, the right wing contacted the runway and terrain. The airplane came to rest upright. Examination of the airplane by Federal Aviation Administration inspectors revealed the airplane hydraulic fluid reservoir contained a minimal amount of fluid (see Figure 1). No visual leaks were noted with the hydraulic system. The reservoir tank was located aft of the firewall and was not visible during a pre-flight inspection due to fuselage structure. The most recent condition inspection was completed on January 12, 2017. The pilot stated he knew the inspection was out of date and was working on getting the inspection completed. Figure 1. Hydraulic Fluid Reservoir - Level Below Minimum (FAA)