Reliable assessment of shorelines extracted from medium-resolution satellite imagery requires independent high-resolution reference data and statistical methods that account for spatial dependence. This study compared three conventional analyst-assisted shoreline-extraction workflows—histogram thresholding, band ratio, and the Normalised Difference Water Index (NDWI)—at Coronation Park, Lake Ontario, Canada, using Sentinel-2 Level-2A imagery. A manually digitised shoreline derived from a UAV-based orthomosaic acquired approximately 27 h before the Sentinel-2 scene served as the independent reference. The UAV-based reference and each Sentinel-2-derived shoreline were divided into 31 ordered segments. For each Sentinel-2-derived segment midpoint, the shortest planar Euclidean distance to the nearest UAV-based reference midpoint was calculated and used to derive mean absolute error (MAE) and root mean square error (RMSE). Residual spatial autocorrelation was assessed using Moran’s I with 9999 permutations. Because the paired differences departed from normality, the Friedman test was treated as the primary overall comparison, while contiguous spatial-block permutation tests across block sizes of two to eight shoreline locations assessed robustness to local spatial dependence. NDWI achieved the highest positional agreement (MAE = 5.645 m; RMSE = 6.429 m), followed by band ratio (MAE = 14.303 m; RMSE = 14.797 m) and histogram thresholding (MAE = 26.167 m; RMSE = 26.910 m). Significant positive residual spatial autocorrelation was identified for all three methods (Moran’s I = 0.587–0.832, all p < 0.001). The Friedman test confirmed a significant extraction-method effect, χ²(2) = 49.226, p < 0.001, Kendall’s W = 0.794, and the effect remained significant across all tested spatial-block sizes, with empirical p-values ranging from 0.000007 to 0.004630. Among the three conventional methods tested at this large-lake site, NDWI provided the highest positional agreement and therefore offers a defensible baseline for evaluating future Sentinel-2 image-enhancement approaches.