This work aims to evaluate how a temporary school square implemented in the city of Bologna under the principles of the tactical urbanism approach impacted on vehicular patterns through exploiting TomTom Floating Car Data (FCD) from before and after the intervention. Such data, passively collected by vehicles acting as moving sensors on the network, have been used for the analyses instead of data collected through usual methods. After statistical validation of available datasets through two-tailed paired Student’s t-tests, trend analyses have been performed on sample sizes and speed-related values to detect global variations in the first place, and more thoroughly among clusters of road segments based on graph-calculated distance from the intervention site. Results suggest that traffic flows have been relocated from segments directly affected by the intervention, where a decrease has been registered (−23.87%), towards adjacent streets or segments in a buffer area, which have recorded an increase (+3.51% and +3.50%, respectively), so the phenomenon of traffic evaporation did not take place as opposed to more widespread tactical urbanism interventions described in the literature. OD matrices per 15-min time fractions over the three selected peak time slots have been extracted in order to obtain reliable input data for a future development of traffic microsimulation models. The extraction method is based on least squares optimization problems solving systems of linear equations representing OD flows assigned to the observed link, after selecting a set of k¯ shortest paths through a Path Size Logit (PSL) model. Even though the availability of large amounts of data could not overcome typical underdetermination of the problem, due to the key issue of data dependence among traffic counts, the validation of retrieved matrices returned good results in terms of correlation between observed and estimated link flows. In the few cases where the quality of correlation fell, underlying causes have been investigated and the influence of outliers, amplified by the high fragmentation of the provided road graph, might represent the core problem.