A major issue with permeable interlocking concrete pavers (PICPs) is clogging of drainage cells. The significant cost of clean-out to restore its function are substantial and discouraging for potential users and municipalities. A rapid clean-out approach using PICPs can address the issue of clogging and restore their long-term functionality. The current investigation employs a novel PICP to optimize the shape of the cupules in order to reduce the clean-out time and cost. A series of experiments were performed on a custom-designed laboratory apparatus. Six independent variables: speed of cleaning equipment over the pavement, the angle of cleaning jets, air velocity in the cleaning jets, the geometry of the cupules, the width of drainage conduit, and gradation of the filter media were selected. The ratio of the mass of removed and captured, relative to the initial mass of cupule filter media (plus filtrate), was selected as a dependent variable. Results demonstrated that high air velocity in the cleaning jet resulted in the most effective percentage of mass removal. This preliminary investigation suggests that rapid clean-out of PICPs could potentially improve the efficiency of the capture of particulates by conventional regenerative-air street cleaning equipment.