The city of Copenhagen currently pursues a very ambitious plan to make the city 'cloudburst proof' within the next 30 years. The cloudburst management plan has the potential to support the city's aim to become more green, liveable, and sustainable. In this study, we assessed stormwater system designs using the Three Point Approach (3PA) as a framework, where an indicator value for each domain was calculated using state-of-the-art modelling techniques. We demonstrated the methodology on scenarios representing sequential enhancements of the cloudburst management plan for a district that has been appointed to become the first climate resilient neighbourhood in Copenhagen. The results show that if the cloudburst system is exploited to discharge runoff from selected areas that are disconnected from the combined sewer system, then the plan leads to multiple benefits. These include improved flood protection under a 100-years storm (i.e., compliance with the new demands in domain C of the 3PA), reduced surcharge to terrain under a 10-years storm (i.e., compliance with the service goal in domain B of the 3PA) and an improved yearly water balance (i.e., better performance in domain A of the 3PA).