The article deals with a diagnosis of multiple leaks from liquid transmission pipelines using analytical methods. Such solutions, based on advanced mathematical models of pipeline flow dynamics, usually turn out to be very complex and time-consuming. However, under certain operating conditions, a simpler approach may also be useful. Such an idea is presented in this paper, proposing two simplified methods for diagnosing double leakages. In principle, these methods apply to both simultaneous and non-simultaneous leaks. The first one uses a static model of a pipeline involving two leaks and takes advantage of the minimization of the objective function defined as the squared deviation of the modeled pressures from the pressures measured on the pipeline. The second method uses a pipeline flow model of a static type in combination with a gradient indicator aimed at detecting leaks and employing algorithms assigned to determining the location and size of leaks. The results of methods’ validation, based on tests carried out with the use of measurement data obtained from an experimental water pipeline, were also presented. The outcomes of the performed tests proved the methods’ effectiveness in terms of detection, isolation, localization, and intensity estimation of both simultaneous and non-simultaneous double leakages.