Transportation services are matched with demand, in multiple segments in accordance with capabilities and business practices of a transportation service provider. A request for transportation services is received, including an origin, destination and a characterization of a load or service. Origin and destination geographical areas or locations are identified, and a main line segment and at least one distinct segment are identified to form a contiguous multi-segment routing. A transportation service provider is matched to the specified demand for transportation services, in order to comply with the scheduled sequence. One or more competitive bids are aggregated to provide a total bid price and provision of the transportation services are arranged using the candidate service interests winning the bid or bids.