A product discharge and delivery system for a vending machine includes a product delivery cup including a carriage portion and a shroud portion having an open bottom section and a discharge element. After receiving a selected product, the product delivery cup is shifted toward a dispensing chamber causing the discharge element to engage with a discharge member mounted within the vending machine. Engagement of the discharge element and discharge member causes the shroud portion to pivot relative to the carrier portion exposing the open bottom section allowing a selected product to release into a dispensing chamber. A delivery port is mounted in the dispensing chamber that rotated between a product receiving position and a product delivery position.