Background: Golf swing performance in medium- to high-handicap players must be reliably measured to use this variable in both research studies and in applied settings. Nevertheless, there are no studies published on this topic and test–retest evidence is only available for low-handicap players. The aim of this study was to determine the number of attempts necessary to obtain a reliable measurement protocol for swing performance variables in medium- to high-handicap players. Methods: Ten amateur players (55.67 (13.64) years, 78.4 (11.4) kg, 1.75 (7.95) m) took part in a test–retest study in two experimental sessions one week apart. In each one, fifteen swings with a six iron and a driver were evaluated with a 3D Doppler tracking golf radar. Results: The results showed that variables related to side carry could not be reliably measured in medium- to high-handicap players in only fifteen trials (ICC < 0.26, SEM > 12.05 m and MDC > 33.41 m). The rest of the performance variables related to the club and ball trajectories could be reliably measured with a 3D Doppler radar with between seven and ten swings. Conclusions: At least seven swings are recommended for the driver and ten for the six iron to measure golf swing performance.