The first public–private partnership (PPP) motorway in Australia was open to traffic more than two decades ago, and yet no comprehensive evaluation of PPPs in the road transport sector has been sighted. It is the intention of this chapter to fill this gap. Although there have been noticeable advancements in contract design and use of incentive mechanisms to optimize risk allocation between the public and private sectors, Australian PPP motorways have yet to deliver an optimal outcome. It is questionable whether the current risk-shifting approach in the present PPP paradigm is suitable for providing infrastructure-based road services where long-term service provision is a requirement. In such cases, a proactive risk management approach may be preferred.