An evaluation method for assessing the difference in the relative humidity (RH) control performance of waterproofing material is proposed. For a demonstration of this evaluation method, two waterproofing materials (urethane coating and cementitious waterproofing material) installed with different methods (positive and negative side of concrete structure respectively) are exposed to temperature conditions representing three seasonal conditions: Summer (40 °C), spring/autumn (20 °C) and winter (4 °C). Condensation level changes on the inner side of the waterproofing material installed specimen is measured, and for derive criteria for comparison, three parameters based on the average RH, intercept RH (derived from a linear regression analysis of RH measurement), and maximum relative humidity are derived for each different waterproofing material installed specimen. Based on quality specification for underground concrete structures, the demonstration evaluation establishes provisional standard criteria of below 70% RH, and all three parameters are evaluated to determine whether the tested waterproofing material/method complies to the performance requirement. Additional analysis through linear regression and cumulative probability density graphs are derived to evaluate the RH consistency and range parameters. The evaluation regime demonstrates a quantitative RH analysis method and apparatus, and a newly designed evaluation criteria is used to compare the RH control performance of positive-side installed urethane waterproofing materials and negative-side installed cementitious waterproofing material.