Leakages can occur in a district heating network, resulting in high economical damage. The propagating pressure wave resulting from large, spontaneous leakages reaches sensors at different locations in the network. This leads to pressure drops registered at each sensor at a different point in time. The time differences help to localize the leakage. Different algorithms are presented and applied in this paper to estimate the pressure drop time points based on non-uniform, time-discrete sensor signals. Five of the nine algorithms are self-developed with, e.g., parts of linear regression, whereas the other four algorithms have already been described in the literature, such as change-point detection. In this paper, several recorded events were investigated, and the algorithms were applied to real measurement data. After detection, leakage localization was performed to determine the affected exclusion area. A performance criterion was used as a measure to compare the algorithms. For practical application, the best-performing algorithm was identified. Furthermore, the events were classified according to how well they could be evaluated.