The invention relates to a system capable of electronically matching transportation reservations with existing, new, or potential reservations, so that the orders can be combined, the reservation shared between requesting parties, utilization and management of transportation provider inventory and costs can be optimized, and savings opportunities for customers may be provided. Costs may also be divided proportionally based on a combination of distance and/or time traveled, or other cost accrual methods per riding party, and split/billed electronically via the reservation system. The system can operate as a standalone reservation repository or in concert with one or many existing reservation providers.