Systems and methods for advertisement-based vehicle matching and routing. For example, a computer-implemented method includes obtaining data associated with a vehicle service request. The data associated with the vehicle service request is indicative of a pick-up location and a destination location associated with the vehicle service request. The method includes determining, from among a plurality of candidate vehicles, a selected vehicle for the vehicle service request based on the data indicative of the vehicle service request, candidate advertisement content items, and candidate routes for the plurality of candidate vehicles. The method includes communicating data that initiates display of a selected advertisement content item by a display device positioned on an exterior of the selected vehicle. The method includes communicating data indicative of route information to a computing device associated with the selected vehicle. The route information includes a selected route to the pick-up location.