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The last decades have seen a tremendous amount of research being devoted to effectively managing vehicle fleets and minimizing empty mileage. However, in contrast to, e.g., the air transport sector, the question of how to best assign crews to vehicles, has received very little attention in the road transport sector. The vast majority of road freight transport in Europe is conducted by single drivers and team driving is often only conducted if there are special circumstances, e.g., security concerns. While it is clear that transport companies want to avoid the costs related to additional drivers, vehicles manned by a single driver sit unused whenever the driver takes a mandatory break or rest. Team drivers, on the other hand, can travel a much greater distance in the same amount of time, because mandatory breaks and rests are required less frequently. This paper investigates under which conditions trucking companies should use single or team driving to maximize their profitability. We present a novel optimization approach for simultaneously optimizing routes and crewing decisions and provide experimental evidence that, for a wide range of cost factors, operating a fleet with a mix of team and single drivers can significantly reduce operational costs when compared to typical profit margins in the sector. [ABSTRACT FROM AUTHOR]