This work validates an analytical single-measurement uncertainty estimator for contour method measurement by comparing it with a first-order uncertainty estimate provided by a repeatability study. The validation was performed on five different specimen types. The specimen types cover a range of geometries, materials, and stress conditions that represent typical structural applications. The specimen types include: an aluminum T-section, a stainless steel plate with a dissimilar metal slot-filled weld, a stainless steel forging, a titanium plate with an electron beam slot-filled weld, and a nickel disk forging. For each specimen, the residual stress was measured using the contour method on replicate specimens to assess measurement precision. The uncertainty associated with each contour method measurement was also calculated using a recently published single-measurement uncertainty estimator. Comparisons were then made between the estimated uncertainty and the demonstrated measurement precision. These results show that the single-measurement analytical uncertainty estimate has good correlation with the demonstrated repeatability. The spatial distributions of estimated uncertainty were found to be similar among the conditions evaluated, with the uncertainty relatively constant in the interior and larger along the boundaries of the measurement plane.