An improved transportation scheduling method for scheduling a plurality of trips T.sub.1 T.sub.n using a plurality of vehicles V1 V.sub.n, each of said plurality of vehicles having a trip manifest. The method comprises the steps of: (a) generating a useability matrix that determines which of said plurality of vehicles V.sub.1 V.sub.n is useable with each of said plurality of trips T.sub.1 T.sub.n; (b) determining a best trip of said plurality of trips T.sub.1 T.sub.n to be scheduled next; (c) determining a best vehicle from said plurality of vehicles V.sub.1 V.sub.n for accommodating said best trip; (d) determining a best insertion pair into said trip manifest of said best vehicle for said best trip and updating said trip manifest to include said best insertion pair; (e) updating said useability matrix to reflect the scheduling of said best trip on said best vehicle; and (f) repeating steps (a) (e) until all of the trips in said plurality of trips T.sub.1 T.sub.n have been scheduled.