Newly installed permeable pavement (PP) systems provide high surface infiltration capacity, but the accumulation of sediments causes a decrease in capacity over time, eventually leading to surface clogging. With the aim of investigating local sedimentation processes and the importance of restorative cleaning (RC), nine recently built PP systems were tested for their infiltration capacity with and without restorative cleaning (RC) over an interval of 12–14.5 months. The results were related to each site’s unique history of sedimentation. RC significantly improved permeability, but when revisited after approximately one year, the permeability of cleaned surfaces was not significantly better for the RC spots than from their uncleaned neighbouring areas. Relating permeability to the contextual issues revealed that PP perimeter, adjacent bare soil and mismanagement strongly affected the sedimentation process. At two of the sites, sedimentation processes were so advanced that surface permeability was below the level of service (five-year design storm).