Water scarcity is a significant global challenge, exacerbated by leakages in water distribution networks. This paper addresses the challenge of detecting leakages in rural and urban–rural water supply systems through hydraulic modelling and a sensitivity analysis. Two distinct real-world network models were studied to assess real and simulated leakage scenarios varying in location and magnitude. A distinct leakage detection approach utilizing outflow measurements from hydrants was tested. Additionally, the effectiveness of various statistical measures—such as correlation, angular closeness, Euclidean distance, Manhattan distance, Chebyshev distance, cosine similarity, and Spearman correlation—were evaluated to determine their efficacy in leakage detection. Different methods for identifying leak candidates were explored and compared, either by selecting a single leak candidate based on similarity measures or by identifying a group of candidates to mark leak hotspots. Density-based spatial clustering of applications with noise was used to assess the number of potential leak candidate groups. The study’s findings contribute to the optimization of leak detection strategies in water supply networks, particularly in rural settings, where detection is challenging due to scarce measurement datasets, budget restrictions, and operational constraints.