Systematical classification of accident factors is very important to take appropriate countermeasures to reduce accidents. The aim of this study is to classify capsizing and sinking factors so as to propose a checklist which could be used to analyze future accidents. The scope is investigation reports of capsizing and sinking accidents published by Japan Transport Safety Board between 2008 and March 2017. The investigation reports were surveyed in order to extract all factors involved in the accidents. Then the factors were categorized into eight classified factors according to their characteristics and a checklist for analyzing capsizing and sinking accidents was proposed. The checklist was applied to capsizing and sinking accidents surveyed in this study and it was revealed that refraining from “navigation in bad weather” is the most effective countermeasure for capsizing and sinking. It was also revealed that “flooding,” whose involvement was the highest for both capsizing and sinking, is the factor which needs countermeasures the most during navigation. It is concluded that accident analyses could be facilitated by applying the proposed checklist to future accidents.