Green Infrastructure (GI) is gaining wide recognition in cooperative research projects seeking to find solutions for climate adaptation in urbanized areas. However, the potential effects of co-produced GI plans and the underlying preparation process are rarely evaluated. To bridge this gap, the aim of this article is to examine what works in addressing environmental burdens in the urban neighborhood of Dortmund Marten, Germany. As part of a larger transdisciplinary process, selective GI measures were delineated in the case study area through a cooperative workshop between scientists and urban planners. Workshop ideas were incorporated into a mitigative scenario considering a hot summer day to quantify the effects of the derived GI measures on thermal comfort and particulate matter dispersion (PM10 and PM2.5). To evaluate the experiences of the science-practice collaboration, the viewpoints of researchers and urban planners on learning effects, knowledge integration, and GI planning were summarized and compared via an online survey. The results indicate that the proposed GI measures could reduce physiological equivalent temperature (PET) by 25 °C. At the same time, additional roadside trees could increase PM10 concentrations by up to 36 µg/m3 due to wind blocking effects. Reflections on the science-practice workshop show that learning effects were higher for the participating researchers than for planning practitioners, while the integration of individual expertise during the workshop was more difficult for academics. These findings point to the importance of continuous reflections on individual understandings in cooperating stakeholder groups and the value of the evaluation of outcomes in transdisciplinary GI planning.