Introduction: This study combined vehicle to vehicle crash frequency and severity estimations to examine factor impacts on Wisconsin highway safety in rainy weather. Method: Because of data deficiency, the real-time water film depth, the car-following distance, and the vertical curve grade were estimated with available data sources and a GIS analysis to capture rainy weather conditions at the crash location and time. Using a negative binomial regression for crash frequency estimation, the average annual daily traffic per lane, the interaction between the posted speed limit change and the existence of an off-ramp, and the interaction between the travel lane number change and the pavement surface material change were found to increase the likelihood of vehicle to vehicle crashes under rainfall. Results: However, more average daily rainfall per month and a wider left shoulder were identified as factors that decrease the likelihood of vehicle to vehicle crashes. In the crash severity estimation using the multinomial logit model that outperformed the ordered logit model, the travel lane number, the interaction between the travel lane number and the slow grade, the deep water film, and the rear-end collision type were more likely to increase the likelihood of injury crashes under rainfall compared with crashes involving only property damage. Practical implications: As an exploratory data analysis, this study provides insight into potential strategies for rainy weather highway safety improvement, specifically, the following weather-sensitive strategies: road design and ITS implementation for drivers' safety awareness under rainfall.