In this study we develop, the first to our knowledge, multiple linear regression model to estimate the effectiveness of the Athens’ traffic restriction scheme called “daktylios”. The utilized data involves traffic flow obtained from 50 measurement stations on road segments inside and outside but close to the restriction zone limits. Multiple linear regression models were designed to explore the parameters affecting traffic flow and traffic flow difference as a result of the scheme’s operation. Results provided insights about the variation of the traffic conditions during the implementation time of the scheme. They demonstrated a slight decrease of traffic flow for sections located inside the restriction zone, indicating the ineffectiveness of the scheme. Furthermore, specific circumstances indicated a variation of drivers’ obedience. For example, the effectiveness of the scheme varied with trip direction (from, to or within the zone), time of day and retail sales. The parameters affecting traffic flow inside the restriction zone were similar throughout the years indicating stabilized driver behavior, with the only exception being the year 2021–2022 during which traffic flow increased probably as a result of travelers’ reluctance to use public transport in fear of COVID-19. The results of the study indicate that the “daktylios” scheme needs to be revisited and probably replaced by more contemporary measures, which address the present needs and behavior of the travelers, and have the potential of being more effective.