Observational methods such as the Asaoka's method and the hyperbolic method are widely applied on the settlement analysis using observed settlement. The most unreliable aspects in those methods is arose from the subjective discretion of initial non-linearity on linear regression. The initial non-linearity is inevitable due to the settlement behaviour itself. Therefore an objective method is essential to achieve more reliable results on settlement analysis. It was found that the initial non-linear data are statistical outliers. New automation algorithms of the hyperbolic and the Asaoka's method were developed based on outlier detection method. The methods are a successive detection of outliers and a searching method of suitable hyperbolic range for the Asaoka's and the hyperbolic method respectively. Applicability of the algorithms was verified through case studies.