Combined sewer overflow (CSO) from urban areas is recognized as a major pollutant source to the receiving waters during wet weather. This study attempts to categorize rainfall events and corresponding CSO behaviours to reveal the relationship between rainfall patterns and CSO behaviours in the Shingashi urban drainage areas of Tokyo, Japan where complete service by a combined sewer system (CSS) and CSO often takes place. In addition, outfalls based on their annual overflow behaviours were characterized for effective storm water management. All 117 rainfall events recorded in 2007 were simulated by a distributed model InfoWorks CS to obtain CSO behaviours. The rainfall events were classified based on two sets of parameters of rainfall pattern as well as CSO behaviours. Clustered rainfall and CSO groups were linked by similarity analysis. Results showed that both small and extreme rainfalls had strong correlations with the CSO behaviours, while moderate rainfall had a weak relationship. This indicates that important and negligible rainfalls from the viewpoint of CSO could be identified by rainfall patterns, while influences from the drainage area and network should be taken into account when estimating moderate rainfall-induced CSO. Additionally, outfalls were finally categorized into six groups indicating different levels of impact on the environment.