Collaborative transportation and logistics pooling are relatively new concepts in research, but are very popular in practice. In the last years, collaborative transportation seems a good city logistics alternative to classical urban consolidation centers, but it is still in a development stage. This chapter proposes a framework for urban logistics pooling ex-ante evaluation. This framework is developed with two purposes. The first is to generate comparable contrasted or progressive scenarios representing realistic situations; the second to simulate and assess them to make a “before-after” comparative analysis. In this framework, a demand generation model is combined with a route optimization algorithm to simulate the resulting routes of the proposed individual or collaborative distribution schemes assumed by each scenario. Then, several indicators are obtained. To illustrate that framework, several scenarios for the urban area of Lyon (France) are simulated and discussed to illustrate the proposed framework possible applications.