This paper explores critical success conditions of collaborative planning projects in the area of urban transport, evaluating the impact of new collaborative methods, instruments and processes on project performance. Hypothesis building is based on a comparative, empirical research design, rather than on deductive theory construction. Potential critical success conditions are derived from literature. Based on five urban transport planning projects in Gothenburg (Sweden), London (United Kingdom), Milwaukee (United States), Tokyo (Japan) and Mexico City (Mexico), a rough set analysis of the five cases reveals validated success conditions, which can be used for formulating hypotheses for further research or for policy and process improvement. The results suggest that a dedicated management of the multi-actor network, a high diversity of actors, as well as an extensive use of knowledge integration methods in combination with a high network density are critical success conditions of these planning processes. Surprisingly, the extensive use of unilateral methods also showed to be an important success condition. The traditional role of the planner will have to be complemented with the expertise of network and methodology management. The authors conclude that rough set analysis can be a valuable addition to narrative, single-case analysis of collaborative urban transport planning processes.