Sudden flooding is one of the major risks for the drainage sinking construction of deep-water caisson. The damage of inner walls due to hydraulic pressure induced by sudden flooding threatens the labor and structural safety. This study developed the numerical model and analytical method to assess the hydraulic pressure on the inner walls of both the balanced and sudden-sinking caisson under sudden flooding risk. An experimental program of sudden flooding into a caisson specimen was conducted in a water basin to validate the numerical model and the analytical method for balanced caisson. The numerical and analytical methods were then illustrated by an actual engineering practice to show the hydraulic pressure on the inner walls for the caisson under balanced and sudden-sinking state, respectively. The experimental validation and engineering illustration prove that the numerical model is effective in the assessment of hydraulic pressure of caisson under sudden flooding, especially for the complicated case that includes the turbulence effect and sudden sinking, while the analytical method can calculate the quasi-static value of the hydraulic pressure more efficiently. The presented methods provide the engineers with alternative tools to learn more about the sudden flooding risk of the deep-water caisson.