This article provides a comparative analysis of the legislative regulation of preventive medical examinations related to the duties of work in the Federal Republic of Germany and the Russian Federation. In particular, the authors researched in most detail the normative framework, the existing types of medical examinations, the limits of permissible examinations, the subject conducting such examinations, as well as the procedure and form of obtaining voluntary informed consent. The study revealed a number of similarities between the two legal systems, as well as significant differences demonstrating the differentiated level of treatment of a particular issue in the various national legislations. For example, it was found that in the Federal Republic of Germany, as in the Russian Federation, the legal framework does not have a single comprehensive act regulating work'related medical examinations. At the same time, the requirements for the special entity performing medical examinations are more specified in German law, while the discussion issue of the limits of doctor’s discretion is more specified in Russian law. The comparative analysis leads to the conclusion that, despite the desire of the legislator in both legal systems to regulate in detail the relations between the employee and the employer in the framework of preventive medical examinations, there are still issues that need to be resolved. Thus, the authors conclude that a number of legislative changes are necessary, in particular, that certain medical examinations that are not related to the performance of the job function are not compulsory in Russian law and that additional safeguards to limit the discretion of the doctor should be provided in German law.